Reaction #1327

Reaction equation

ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate

Compound 1

ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate

sodium borohydride

→

title compound

Ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-naphth-2-yl) ethynyl]benzoate

Solvents

water

THF

ethanol

Conditions

Workup

1. 1
   Extractionextracted with Et2O (4×40 ml)
2. 2
   WashThe combined organic layers were washed with 10% HCl (5 ml), 10% aqueous NaHCO3 (10 ml) and brine (20 ml)
3. 3
   Dryingdried over MgSO4
4. 4
   Concentrationconcentrated in vacuo

Procedure

To a cold solution (0° C.) of 980 mg (2.8 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 5 ml of THF and 10 ml of ethanol was added 78 mg (2 mmol) of sodium borohydride. The mixture was stirred for 6 hours, diluted with water (10 ml) and extracted with Et2O (4×40 ml). The combined organic layers were washed with 10% HCl (5 ml), 10% aqueous NaHCO3 (10 ml) and brine (20 ml), dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid.

Source