Hydrochloric Acid → HCID 22118303, compound

Participants

Reaction Steps

A solution of 1M diethyl zinc in n-hexane(1.4 ml) was added to a solution of 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2,5-dimethyl-hex-5-en-3-ol (0.40 g) in dichloromethane at 20° C. Diiodomethane (0.13 ml) was then added and the mixture stirred and heated at reflux for 2 hours. Hydrochloric acid (1N) was added and the organic layer washed with brine, dried (magnesium sulphate), and evaporated to give crude 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-4-(1-methylcyclopropyl)-butan-3-ol. Powdered molecular sieve 4A (3 g) and pyridinium chlorochromate (0.6 g) were added to a stirred dichloromethane solution of the above compound at 20° C. After 3 hours, ether was added and the mixture filtered, evaporated and purified by silica gel column chromatography, eluting with n-hexane/ethyl acetate (3:1) to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-4-(1-methylcyclopropyl)butan-3-one (Compound 1066, 0.25 g), NMR: 1.33(4H), 1.08(s,3H), 1.42(s,6H), 1.92(s,3H), 2.47(s,2H), 5.26(s,2H), 7.20-7.40(5H).

Provenance & Evidence