Dimethyl Sulfoxide → HCID 54005066, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.9 ml (30.6 mmole) of oxalyl chloride in 80 ml of CH2Cl2 at -50° C. was added a solution of 4.74 ml (61.2 mmole) of DMSO in 14.0 ml of CH2Cl2. This mixture was then stirred at -50° C. for another 5 minutes and added slowly with 4.1 g (15.3 mmole) of (R)-3-[3-(acetyloxy)propyl]-2-methyl-1-cyclohexene-1-butanol in 16.3 ml of CH2Cl2. The mixture was then stirred at -50° C. for another 35 minutes and added with 20.0 ml (143 mmole) of triethylamine to give a white suspension. After stirring at -50° C. for 5 minutes, the mixture was stirred at room temperature for 10 minutes, added with 20 ml of water and extracted with 2×300 ml of CH2Cl2. The combined extracts were then washed with 2×50 ml of water, brine, dried over Na2SO4, filtered and concentrated. The crude product was chromatographed on a silica gel column (6:1, hexane/EtOAc) to give 3.6 g (87.8%) of the unstable (R)-3-[3-(acetyloxy)propyl]-2-methyl-1-cyclohexene-1-butanal as an oil. [α]D25 =-17.11° (CHCl3, c=1.04). IR (CHCl3): 1725, 2725 cm-1. 1H NMR (200 MHz): δ1.25 (m, 1H), 1.61 (s, 3H), 1.56-1.75 (m, 10H), 1.91 (n, 2H), 2.05 (s, 3H), 1.95-2.10 (m, 2H), 2.40 (dt, J=1.8, 7.3 Hz, 2H), 4.06 (m, 2H), 9.77 (t, J=1.8 Hz, 1H). Mass spectrum: M+ (266). Anal. for C16H26O3 : Calc. for C, 72.14; H, 9.80. Found: C, 70.12; H, 9.72.

Provenance & Evidence