Methanol → HCID 71231030, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 34.0 g (97.0 mmol) of 6-tert-butyl-5-isobutoxy-2-methyl-4-phenylindan-1-one in 300 ml of THF cooled to 5° C. 5.00 g (132 mmol) of NaBH4 was added. Further on, 150 ml of methanol was added dropwise to this mixture by vigorous stirring for ca. 7 h at 5° C. The resulting mixture was evaporated to dryness, and the residue was partitioned between 500 ml of dichloromethane and 500 ml of 1 M HCl. The organic layer was separated, the aqueous layer was additionally extracted with 100 ml of dichloromethane. The combined organic extract was evaporated to dryness to give a colorless oil. To a solution of this oil in 500 ml of toluene 1 g of TsOH was added, and this mixture was refluxed with Dean-Stark head for 15 min and then cooled to room temperature using a water bath. The resulting solution was washed by 10% aqueous Na2CO3. The organic layer was separated, the aqueous layer was extracted with 2×100 ml of dichloromethane. The combined organic solution was dried over K2CO3 and then passed through a short pad of silica gel 60 (40-63 um). The silica gel pad was additionally washed by 100 ml of dichloromethane. The combined organic elute was evaporated to dryness. This procedure gave 32.4 g (99%) of 5-tert-butyl-6-isobutoxy-2-methyl-7-phenyl-1H-indene which was further used without an additional purification.

Provenance & Evidence