Methanol → HCID 118040555, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 653 mg (1.4 mmol) of the compound from Example 2A were dissolved in 12 ml of dichloromethane and the mixture was cooled to 0° C. 4.6 ml (4.6 mmol) of a 1 M solution of boron tribromide in dichloromethane were slowly added dropwise and the mixture was stirred at 0° C. for another 4 h (clear yellow solution). 7 ml of abs. methanol were then added and the mixture was heated under reflux overnight. The mixture was then concentrated to dryness under reduced pressure and the residue was partitioned between ethyl acetate and 10% strength aqueous sodium carbonate solution. The aqueous phase was re-extracted with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulphate. After concentration, the residue (519 mg of a brown oil) was purified by column chromatography on silica gel (mobile phase: gradient isohexane/4-32% ethyl acetate).

Provenance & Evidence