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Notes and references
{ A solution of DHAD or GLAD (1.25 mmol (5 2.5 mmol based on
[DHA] or [GLA])), metal catalyst (0.25 mmol based on [metal]) in alcohol
(4 mL) was heated at 90 uC for 1 h – several h as shown in Table 1. The
reaction mixture was cooled to room temperature, followed by GLC
analysis using a Shimadzu GC-14A gas chromatograph with a 30 m 6
0.25 mm glass capillary column (DB-FFAP) and GC-MS analysis using a
Shimadzu QP-5050A mass spectrometer with a Shimadzu GC-17A gas
chromatograph (using Stabilwax-DA as a glass capillary column).
{ CH3C(OMe)2CH(OMe)2: 1H NMR (400 MHz, CD3OD, 25 uC, TMS)
d 4.23 (s, 1H, –CH–), 3.48 (s, 6H, –OMe), 3.35 (s, 6H, –OMe), 1.20 (s, 3H,
–Me), 13C NMR (100 MHz, CD3OD, 25 uC) d 107.2 (–CH–), 67.8 (–C–),
57.7 (–OMe), 49.8 (–OMe), 16.6 (–Me); GC-MS analysis m/z 5 149 [M 2
Me]+, 133 [M 2 OMe]+, 89 [M 2 CH(OMe)2]+. The H and 13C NMR
1
spectra were measured using JEOL JNM-AL400 and Varian INOVA-400
spectrometers. This compound can be converted to pyruvic aldehyde
dimethylacetal only by purification of the reaction mixture through a SiO2
short-pad.24,25 Note that this species appears at a retention time close to
that of methyl lactate under the GLC and GC-MS equipment described
above.
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2718 | Chem. Commun., 2005, 2716–2718
This journal is ß The Royal Society of Chemistry 2005