Page 19 of 23
The Journal of Organic Chemistry
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Hz, 1H), 2.17–2.08 (m, 1H), 1.96–1.92 (m, 1H), 1.74–1.66 (m, 2H), 1.63 (s, 3H), 1.62 (s, 3H). 13C{1H} NMR (125
MHz, DMSO-d6): δ 157.4, 149.5, 141.0, 138.8, 130.9, 129.3, 127.5, 126.9, 126.6, 116.9, 110.3, 105.5, 44.1, 36.1,
30.8, 29.9, 23.8, 19.7. HRMS (ESI): calcd for C22H23O2 [M – H]–, 319.1704; found, 319.1700. IR(neat): 3435br,
3069m, 3034w, 2922s, 2855m, 2832w, 2358s, 2340m, 1643m, 1621m, 1641w, 1587m, 1572m, 1567w, 1461m,
1453m, 1426w, 1415w, 1346w, 1305w, 1274w, 1240w, 1189w, 1052w, 1027m, 890w, 846w, 761m, 696m, 668w,
652w, 546w, 424w.
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(1'R,2'R)-5'-methyl-2'-(prop-1-en-2-yl)-4-vinyl-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol (6j). Following
the general procedure described above and starting from 4ej (87.7 mg, 0.2 mmol), the title compound 6j was
prepared as an off-white solid (48.6 mg, 90% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.92 (br, 2H), 6.49–6.42
(m, 1H), 6.28 (s, 2H), 5.51–5.47 (d, J = 17.6 Hz, 1H), 5.11–5.10 (m, 2H), 4.49 (m, 1H), 4.41 (m, 1H), 3.87–3.85
(m, 1H), 3.05 (td, td, J = 12.2, 2.8 Hz, 1H), 2.11–2.08 (m, 1H), 1.95–1.90 (m, 1H), 1.70–1.67 (m, 2H), 1.60 (s, 3H),
1.59 (s, 3H). 13C{1H} NMR (125 MHz, DMSO-d6): δ 157.2, 149.5, 137.6, 135.6, 130.8, 126.8, 117.7, 112.8, 110.2,
105.0, 44.1, 36.2, 30.8, 29.8, 23.8, 19.6. HRMS (ESI): calcd for C18H21O2 [M – H]–, 269.1547; found, 269.1545.
IR(neat): 3423s, 2964s, 2924s, 1624m, 1577m, 1511w, 1493m, 1439m, 1376w, 1312w, 1274w, 1238w, 1217w,
1150w, 1054w, 1026m, 985w, 891w, 847w, 550w. MP: 62.5–65.5 °C.
(1'R,2'R)-5'-methyl-2'-(prop-1-en-2-yl)-4-(prop-1-yn-1-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol (6k).
Following the general procedure described above and starting from 4ek (90.1 mg, 0.2 mmol), the title compound
6k was prepared as an off-white solid (54.1 mg, 96% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.03 (br, 2H), 6.20
(s, 2H), 5.07 (s, 1H), 4.47 (m, 1H), 4.41 (m, 1H), 3.86–3.83 (m, 1H), 3.02 (td, J = 11.8, 2.8 Hz, 1H), 2.13–2.07 (m,
1H), 1.97 (s, 3H), 1.96–1.90 (m, 1H), 1.70–1.64 (m, 2H), 1.60 (s, 3H), 1.58 (s, 3H). 13C{1H} NMR (125 MHz,
DMSO-d6): δ 157.0, 149.4, 130.9, 126.5, 121.2, 118.3, 110.3, 109.9, 84.8, 80.5, 44.0, 36.2, 30.8, 29.8, 23.7, 19.6,
4.3. HRMS (ESI): calcd for C19H21O2 [M – H]–, 281.1547; found, 281.1544. IR(neat):3407s, 3328s, 2931s, 1622m,
1571s, 1519w, 1434m, 1426m, 1377w, 1345w, 1310w, 1294w, 1243m, 1169m, 1049w, 1031w, 1023w, 966w, 903w,
874w, 847m, 828m, 634w, 607w, 542w, 516w. MP: 131.2–133.7 °C.
(1'R,2'R)-5'-methyl-2'-(prop-1-en-2-yl)-4-(pyridin-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol
(6l)
Following the general procedure described above and starting from 4el (979 mg, 2 mmol), the title compound 6l
was prepared as a brown solid (585 mg, 91% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.08 (s, 2H), 8.65–8.53 (m,
1H), 7.82 (td, J = 7.7, 1.9 Hz, 1H), 7.63 (dd, J = 8.1, 1.1 Hz, 1H), 7.30–7.23 (m, 1H), 6.93 (s, 2H), 5.14 (s, 1H),
4.52 (d, J = 2.8 Hz, 1H), 4.43 (dd, J = 3.0, 1.6 Hz, 1H), 3.95–3.90 (m, 1H), 3.15–3.04 (m, 1H), 2.13–2.08 (m, 1H),
1.97–1.92 (m 1H), 1.73–1.64 (m, 2H), 1.62 (s, 6H). 13C{1H} NMR (125 MHz, DMSO): δ 157.4, 156.7, 149.8,
149.4, 137.5, 137.3, 130.9, 126.7, 122.6, 119.9, 118.7, 110.3, 105.4, 44.1, 36.2, 30.8, 30.1, 29.8, 23.8, 19.6. HRMS
(ESI): calcd for C21H24NO2 [M + H]+, 322.1802; found, 322.1809. IR(neat): 3418br, 3069w, 2964s, 2923m,
1643w, 1622w, 1585m, 1563m, 1472m, 1443m, 1376w, 1346w, 1283w, 1252w, 1193w, 1154w, 1054w, 1031w,
1002w, 899w, 858w, 783m, 752w, 678w. MP: 85.1–86.9 °C.
(1'R,2'R)-4-(5-chlorothiophen-2-yl)-5'-methyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-d
iol (6m). Following the general procedure described above and starting from 4em (106 mg, 0.2 mmol), the title
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compound 6m was prepared as a vitreous solid (70.8 mg, 98% yield). H NMR (400 MHz, DMSO-d6): δ 9.18 (s,
2H), 7.08 (d, J = 3.9 Hz, 1H), 7.05 (d, J = 3.9 Hz, 1H), 6.41 (s, 2H), 5.10 (s, 1H), 4.51 (m, 1H), 4.43 (m, 1H),
3.90–3.86 (m, 1H), 3.05 (td, J = 11.5, 2.9 Hz, 1H), 2.18–2.09 (m, 1H), 1.96–1.91 (m, 1H), 1.73–1.61 (m, 2H), 1.60
(d, J = 2.3 Hz, 6H). 13C{1H} NMR (125 MHz, DMSO): δ 157.6, 149.4, 143.5, 131.2, 131.0, 128.5, 126.7, 126.5,
122.5, 118.1, 110.3, 104.1, 44.1, 36.2, 31.2, 30.8, 29.8, 23.7, 19.5. HRMS (ESI): calcd for C20H22ClO2S [M + H]+,
361.1024; found, 361.1023. IR(neat):3414br, 3070w, 2964w, 2923s, 2830w, 2360m, 2341m, 1623m, 1577m,
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