Tetrahydrofuran → (1S)-5-bromo-2,3-dihydro-1H-inden-1-ol

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with 5-bromo-1-indanone (50.0 g, 0.24 mol), anhydrous THF (500 mL) and (R)-methyl-CBS-oxazaborolidine (10.0 g, 0.04 mol) and the solution was heated to 35° C. under N2. Borane-methylsulfide (10.0 M, 650 mL, 6.5 mol) was added dropwise over 1.5 hours. The mixture was stirred at 35° C. for 1 hour. Upon consumption of the starting material (TLC analysis), the reaction was cooled to 0° C. and was quenched with water (200 mL) at such a rate to maintain the reaction temperature below 5° C. The mixture was extracted with EtOAc (4×200 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to give a yellow solid. The solids were dissolved in hot CHCl3 (150 mL) and hexane (300 mL) and upon cooling to room temperature solids precipitated from the solution. After further cooling at 0° C., the solids were collected by vacuum filtration to afford (S)-5-bromo-indan-1-ol (22 g, 44%) as a light-yellow solid. This material was carried on to the next step without further purification.

Provenance & Evidence