Hydrochloric Acid → HCID 67984570, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 19.7 g of 6-tert-butyl-2-(2,2-dimethylpropyl)-5-methoxy-4-phenyl-1-indanone of 93% purity (50.3 mmol), 15.0 g of NaBH4, and 200 ml of THF 100 ml of water was slowly (for ca. 10 h) added by vigorous stirring at 5° C. The resulting mixture was stirred overnight at room temperature. Further on, 500 ml of cold water was added, the resulting mixture was acidified by 12 N HCl to pH 1, and then the crude product was extracted with 3×150 ml of dichloromethane. To a solution of the residue in 300 ml of toluene 0.5 g of TsOH was added, the resulting mixture was refluxed for 15 min with Dean-Stark head, then quickly cooled to room temperature, and treated with 50 ml of 10% aqueous K2CO3 to remove acidic impurities. The organic layer was separated, the aqueous layer was extracted with 2×75 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-64 um, 450 m3 of silica gel, eluent: hexanes-dichloromethane=4:1, vol.). Yield 17.3 g (99%) of the title product as yellowish oil.

Provenance & Evidence