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d=157.9, 131.9, 129.5, 128.7, 128.3, 122.4, 121.5, 115.1, 87.2, 84.0,
56.7 ppm.
tography. 1H NMR (500 MHz, CDCl3): d=7.49 (d, J=7.5 Hz, 4H),
7.40 (t, J=7.6 Hz, 4H), 7.32 (t, J=7.3 Hz, 2H), 7.27 (t, J=8.0 Hz,
2H), 7.03 (d, J=8.0 Hz, 2H), 6.97 (t, J=7.4 Hz, 1H), 6.28 ppm (s,
1H). 13C NMR (126 MHz, CDCl3): d=158.3, 141.4, 129.4, 128.7, 127.8,
127.0, 121.1, 116.3, 81.9 ppm.
N-(4-(4-Fluorophenyl)-6-isopropyl-5-(phenoxymethyl)pyrimidin-
2-yl)-N-methylmethanesulfonamide (3r). White solid (86.2 mg,
>99%, Procedure B; 1.48 g from a 3.5 mmol scale, 97%), a mix-
ture of petroleum ether/ ethyl acetate=40/ 1 (v/ v) as eluents for
column chromatography. M.p.: 152.4–155.18C. 1H NMR (500 MHz,
CDCl3): d=7.75 (m, 2H), 7.34 (m, 2H), 7.10 (tm, J=8.7 Hz, 2H), 7.05
(t, J=7.4 Hz, 1H), 6.96 (d, J=7.9 Hz, 2H), 4.91 (s, 2H), 3.61 (s, 3H),
3.54 (s, 3H), 3.36 (m, 1H), 1.34 ppm (d, J=6.7 Hz, 6H). 19F NMR
(471 MHz, CDCl3): d=À110.9 ppm (m, 1F). 13C NMR (126 MHz,
CDCl3): d=178.4, 166.6, 163.8 (d, J=250.5 Hz), 158.4, 158.0, 133.8
(d, J=3.2 Hz), 131.5 (d, J=8.2 Hz), 129.7, 121.6, 117.5, 115.6 (d, J=
21.8 Hz), 114.7, 63.3, 42.5, 33.1, 31.8, 22.1 ppm. IR (KBr): n=3117,
3077, 3041, 3013, 2977, 2929, 2901, 2872, 1603, 1554, 1509, 1496,
1484, 1441, 1403, 1363, 1335, 1230, 1152, 1068, 1026, 994, 965,
(3aS,5S,6R,6aS)-5-((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-di-
methyl-6-phenoxytetrahydrofuro[2,3-d][1,3]dioxole (3x). White
solid (61.2 mg, 91%, Procedure B), a mixture of petroleum ether/
ethyl acetate=40/ 1 (v/ v) as eluents for column chromatography.
M.p.: 101–103.28C. a23:5 =À44.44 (c=0.676 g/100 mL, CHCl3).
D
1H NMR (500 MHz, CDCl3): d=7.32 (t, J=7.9 Hz, 2H), 7.02–6.98 (m,
3H), 5.94 (d, J=3.8 Hz, 1H), 4.74 (d, J=3.0 Hz, 1H), 4.61 (d, J=
3.8 Hz, 1H), 4.48 (dd, J=13.0 Hz, J=6.1 Hz, 1H), 4.35 (dd, J=
7.5 Hz, J=3.1 Hz, 1H), 4.17–4.11 (m, 2H), 1.56 (s, 3H), 1.45 (s, 3H),
1.33 (s, 3H), 1.31 ppm (s, 3H). 13C NMR (126 MHz, CDCl3): d=156.9,
129.7, 121.8, 115.5, 112.1, 109.1, 105.3, 82.2, 80.5, 79.8, 72.3, 67.0,
26.8, 26.8, 26.3, 25.3 ppm. IR (KBr): n=3063, 3041, 2987, 2935,
2879, 1601, 1588, 1498, 1470, 1456, 1381, 1371, 1291, 1246, 1173,
948, 898, 872, 846, 821, 774, 763, 729, 711, 693, 630, 603 cmÀ1
.
HRMS-ESI (m/z) calcd for C22H25FN3O3S ([M+H]+): 430.1595; found:
1157, 1078, 1054, 976, 884, 847, 815, 755, 692 cmÀ1 HRMS-ESI (m/z)
430.1595.
.
calcd for C18H25O6 ([M+H]+): 337.1646; found: 336.1636.
(3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyl-3a-(phenoxymethyl)tetra-
hydro-5H-bis([1,3]dioxolo)[4,5-b:4’,5’-d]pyran (3s). Light yellow
oil (61. 6 mg, 96%, Procedure B), a mixture of petroleum ether/
ethyl acetate=20/ 1 (v/ v) as eluents for column chromatography.
(3s,5s,7s)-1-Phenoxyadamantane (3y).[23] White solid (1.4 mg,
3%, Procedure A; 26.8 mg from NaH (12.0 mg, 0.3 mmol, 60%) as
a base, 59%), a mixture of petroleum ether/ ethyl acetate=80/ 1
(v/ v) as eluents for column chromatography. M.p.: 108.0–110.48C.
1H NMR (500 MHz, CDCl3): d=7.28 (t, J=7.5 Hz, 2H), 7.12 (t, J=
7.3 Hz, 1H), 7.02 (d, J=7.6 Hz, 2H), 2.20 (brs, 3H), 1.91 (d, J=
2.1 Hz, 6H), 1.64 ppm (m, 6H). 13C NMR (126 MHz, CDCl3): d=153.0,
127.6, 124.0, 122.6, 76.6, 41.8, 35.1, 29.8 ppm.
a23:5 =À15.93 (c=0.676 g/100 mL, CHCl3). 1H NMR (500 MHz,
D
CDCl3): d=7.39 (tm, J=8.0 Hz, 2H), 6.98–6.93 (m, 3H), 4.65 (dd, J=
7.9 Hz, J=2.6 Hz, 1H), 4.57 (d, J=2.6 Hz, 1H), 4.27 (dd, J=7.8 Hz,
J=1.2 Hz, 1H), 4.16 (d, J=10.1 Hz, 1H), 4.05 (d, J=10.1 Hz, 1H),
3.98 (dd, J=13.0 Hz, J=1.9 Hz, 1H), 3.80 (d, J=13.0 Hz, 1H), 1.58
(s, 3H), 1.51 (s, 3H), 1.50 (s, 3H), 1.35 ppm (s, 3H). 13C NMR
(126 MHz, CDCl3): d=158.6, 129.4, 121.1, 114.7, 109.0, 108.9, 102.3,
71.1, 70.3, 70.1, 68.8, 61.2, 26.6, 26.0, 25.4, 24.1 ppm. IR (KBr): n=
3064, 3041, 2990, 2936, 1601, 1589, 1497, 1456, 1381, 1373, 1337,
1301, 1250, 1215, 1184, 1165, 1105, 1071, 1050, 1015, 981, 914, 891,
868, 837, 816, 754, 715, 691, 673, 637 cmÀ1. HRMS-ESI (m/z) calcd
for C18H25O6 ([M+H]+): 337.1646; found: 337.1654.
N-(2-Phenoxyethyl)aniline (3z).[24] Yellow solid (9.3 mg, 22%, Pro-
cedure B; 23.7 mg from 2a ([Ph3S][OTf], 247.2 mg, 0.6 mmol), 1z
(12.3 mg, 0.2 mmol) and CsOH (90.0 mg, 0.6 mmol), 56%), a mix-
ture of petroleum ether/ ethyl acetate=40/ 1 (v/ v) as eluents for
column chromatography. M.p.: 48.8–49.38C. 1H NMR (500 MHz,
CDCl3): d=7.32 (t, J=7.7 Hz, 2H), 7.23 (t, J=7.6 Hz, 2H), 7.00 (t, J=
7.4 Hz, 1H), 6.96 (d, J=8.0 Hz, 2H), 6.77 (t, J=7.3 Hz, 1H), 6.71 (d,
J=7.9 Hz, 2H), 4.19 (t, J=5.3 Hz, 2H), 4.12 (brs, 1H), 3.56 ppm (t,
J=5.3 Hz, 2H). 13C NMR (126 MHz, CDCl3): d=158.7, 147.9, 129.6,
129.4, 121.1, 117.9, 114.6, 113.2, 66.4, 43.4 ppm.
(R)-2,2-Dimethyl-4-(phenoxymethyl)-1,3-dioxolane (3t). Light
yellow oil (36.8 mg, 88%, Procedure B), a mixture of petroleum
ether/ ethyl acetate=40/ 1 (v/ v) as eluents for column chromatog-
1
raphy. a25 =À27.20 (c=0.500 g/100 mL, Et2O). H NMR (500 MHz,
D
CDCl3): d=7.29 (t, J=7.7 Hz, 2H), 6.97 (t, J=7.3 Hz, 1H), 6.93 (d,
J=8.0 Hz, 2H), 4.49 (m, 1H), 4.18 (t, J=6.8 Hz, 1H), 4.07 (m, 1H),
3.96–3.90 (m, 2H), 1.48 (s, 3H), 1.42 ppm (s, 3H). 13C NMR
(126 MHz, CDCl3): d=158.6, 129.5, 121.1, 114.6, 109.7, 74.1, 68.8,
66.9, 26.8, 25.4 ppm. HRMS-ESI (m/z) calcd for C12H17O3 ([M+H]+):
209.1172; found: 209.1173.
N-(2-Phenoxyethyl)-N-phenylaniline (3z’). Trace, Procedure B;
11.1 mg from 2a ([Ph3S][OTf], 247.2 mg, 0.6 mmol), 1z (12.3 mg,
0.2 mmol) and CsOH (90.0 mg, 0.6 mmol), 19%), a mixture of petro-
leum ether/ ethyl acetate=80/ 1 (v/ v) as eluents for column chro-
1
matography. H NMR (500 MHz, CDCl3): d=7.28–7.23 (m, 6H), 7.06
(d, J=7.9 Hz, 4H), 6.98–6.91 (m, 3H), 6.85 (d, J=8.0 Hz, 2H), 4.19–
4.13 ppm (m, 4H). 13C NMR (126 MHz, CDCl3): d=158.7, 147.8,
129.5, 129.4, 121.6, 121.0, 120.9, 114.5, 64.8, 51.2 ppm. IR (KBr): n=
3060, 3037, 2924, 2871, 2853, 1598, 1588, 1576, 1496, 1475, 1461,
1362, 1300, 1242, 1172, 1154, 1098, 1078, 1056, 1040, 993, 885,
865, 818, 800, 750, 692 cmÀ1. HRMS-ESI (m/z) calcd for C20H19NOK
([M+K]+): 328.1098; found: 328.1099.
(Cyclohexyloxy)benzene (3u).[21] Colorless oil (7.0 mg, 20%, Proce-
dure A; 38.8 mg from a 1.0 mmol scale of 1u (100.2 mg), 22%;
13.0 mg from NaH (12.0 mg, 0.3 mmol, 60%) as a base, 37%).
1H NMR (500 MHz, CDCl3): d=7.29 (t, J=7.5 Hz, 2H), 6.96–6.93 (m,
3H), 4.27 (m, 1H), 2.01 (m, 2H), 1.83 (m, 2H), 1.62–1.52 (m, 3H),
1.44–1.33 ppm (m, 3H). 13C NMR (126 MHz, CDCl3): d=157.9, 129.4,
120.5, 116.2, 75.4, 31.9, 25.7, 23.8.
4-Phenoxybutan-2-ol (3aa).[25] Light yellow oil (58.4 mg from a
0.4 mmol scale of 1aa (36.2 mg), 88%), a mixture of petroleum
ether/ ethyl acetate=80/ 1 (v/ v) as eluents for column chromatog-
(3-Phenoxybutyl)benzene (3v).[23] Brown oil (28.5 mg, 63%, Proce-
dure B), a mixture of petroleum ether/ ethyl acetate=80/ 1 (v/ v)
1
1
raphy. H NMR (500 MHz, CDCl3): d=7.29 (tm, J=8.0 Hz, 2H), 6.96
as eluents for column chromatography. H NMR (500 MHz, CDCl3):
(t, J=7.3 Hz, 1H), 6.92 (d, J=8.0 Hz, 2H), 4.17 (m, 1H), 4.10 (m,
2H), 2.31 (brs, 1H), 1.93 (m, 2H), 1.28 ppm (d, J=6.3 Hz, 3H).
13C NMR (126 MHz, CDCl3): d=158.7, 129.5, 120.9, 114.6, 66.3, 65.8,
38.2, 23.7 ppm.
d=7.26–7.23 (m, 4H), 7.19–7.16 (m, 3H), 6.92 (t, J=7.2 Hz, 1H),
6.86 (d, J=8.0 Hz, 2H), 4.35 (m, 1H), 2.76 (m, 2H), 2.06 (m, 1H),
1.88 (m, 1H), 1.31 ppm (d, J=6.0 Hz, 3H). 13C NMR (126 MHz,
CDCl3): d=158.2, 141.9, 129.5, 128.5, 128.4, 125.9, 120.6, 116.0,
72.8, 38.3, 31.9, 19.8 ppm.
(Phenoxymethylene)dibenzene (3w).[21] Light yellow oil (49.2 mg,
94%, Procedure A), petroleum ether as eluent for column chroma-
Oxydibenzene (3ab).[16] Colorless oil (27.2 mg, 80%, Procedure A),
petroleum ether as eluent for column chromatography. 1H NMR
(500 MHz, CDCl3): d=7.35 (t, J=7.9 Hz, 4H), 7.12 (t, J=7.4 Hz, 2H),
Chem. Asian J. 2019, 14, 3370 –3379
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