Sulfuric Acid → 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhex-5-en-3-one

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Reaction Steps

Chromic acid [1.7 ml of a solution prepared by the addition of a solution of sodium dichromate (0.4 g) in water (1.2 ml) to concentrated sulphuric acid (0.54 ml) and diluted to 2 ml with water] was added dropwise at 25° C. to a stirred solution of 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhex-5-ene-3-ol (1.0 g) in ether. After 18 hours the ether layer was separated, washed with sodium bicarbonate solution (2N) and with brine, dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica gel eluting with dichloromethane, to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhex-5-en-3-one (Compound 7, 0.12 g) as a yellow oil, NMR 1H δ1.4(s,6H), 1.88(s,3H), 3.22(d,2H), 5.05(m,2H), 5.22(s,2H), 5.9(m.1H), 7.2-7.35(m,5H).

Provenance & Evidence