Dimethyl Sulfoxide → HCID 67820272, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.51 mL, 5.8 mmol) in 14 mL methylene chloride was cooled to -60° C. in a dry ice/chloroform bath. Dimethyl sulfoxide (0.9 mL, 11.7 mmol) in 1.0 mL methylene chloride was added and the reaction mixture was stirred for 3 minutes. The alcohol resulting from Example 8A (1.0 g, 5.31 mmol) in 2.0 mL of methylene chloride was added in one portion maintaining the temperature at -40° C. After 15 minutes, triethylamine (3.7 mL, 26.6 mmol) was added dropwise and the mixture was stirred for 5 minutes, warmed to ambient temperature, and N,N-dimethylhydrazine (1.61 mL, 1.28 g, 21.2 mmol) and magnesium sulfate (1.3 g) were added. The mixture was stirred for 1 hour at ambient temperature. Water (100 mL) was added and the organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and filtered. Evaporation of the filtrate gave the hydrazone as a yellow oil. The crude hydrazone was purified by silica gel chromatography using (7:93) ethyl acetate:hexane to afford 808 mg (62%) of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 0.90 (d, J=6 Hz, 3H), 0.95 (d, J=6 Hz, 3H), 1.29-1.19 (m, 1H), 1.38 (s, 3H), 1.53-1.42 (m,s, 4H), 1.85-1.67 (bm, 1H), 2.82 (s, 6H), 4.33-4.25 (m, 1H), 4.6 (dd, J=7,8 Hz, 1H), 6.41 (d, J=6 Hz, 1 H). MS (DCI/NH3) m/e 229 (M+H)+.

Provenance & Evidence