Methanol → HCID 10889806, compound

Participants

Reaction Steps

In a stream of nitrogen gas, 8.8 g of (3aR, 7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one was dissolved in 100 ml of dichloromethane, and 95 ml of dichloromethane solution of boron tribromide (1M-CH2Cl2 solution) was slowly added dropwise to the mixture while the mixture was being cooled by ice. Thereafter, the mixture was stirred for 24 hours at room temperature, the resultant mixture was cooled by ice, and then 60 ml of methanol was added extremely slowly thereto, in dropwise fashion. The mixture was refluxed for 3 hours. The resultant mixture was cooled by ice, and 50 ml of saturated sodium bicarbonate solution was added slowly thereto to separate the organic layer. The organic layer was washed with saturated sodium bicarbonate solution and water, and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated, and the residue was distilled under a reduced pressure. Thus, 13.0 g of the titled compound was obtained.

Provenance & Evidence