Triethylamine → 7-Allyl-6-methoxy-1,4-dihydrobenz[d][1,3]oxazin-2-one

Participants

Reaction Steps

677 mg of 2-amino-5-methoxy-4-(2-propenyl)benzylalcohol was dissolved in 20 ml of tetrahydrofuran under nitrogen atmosphere. Thereafter, 0.52 g of triphosgene and 1.46 ml of triethylamine were added to the reaction solution while cooling on ice. The obtained mixture was then stirred at room temperature for 30 minutes. Thereafter, while cooling on ice, water and ammonia water were added to the reaction solution until foaming was terminated. The reaction solution was diluted with ethyl acetate and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) and then reprecipitated from ethyl acetate, so as to obtain 485 mg of the subject compound.

Provenance & Evidence