Benzyl Bromide → HCID 19366823, compound

Participants

Reaction Conditions

Reaction Steps

Part A: To a solution of 5.0 g (22 mmol) of 3-[(4-methoxyphenyl)sulfonyl]propan-1-ol from example 13 and 6 mL of DMPU in 100 mL of anhydrous THF at -70° C. under nitrogen, was added 5.7 mL (2.8 g, 43 mmol) of a 10.0 M solution of n-butyllithium in hexane. After stirring for 30 min. at -70° C., 2.3 mL (3.3 g, 20 mmole) of benzyl bromide was added. After 18 hours, the reaction mixture was cooled to zero° C. and 25 mL of saturated ammonium chloride solution was added, followed by ethyl acetate and water, the layers were separated and the aqueous layer was extracted 2×s with ethyl acetate. The 3 organic layers were combined and washed with brine, dried with magnesium sulfate, filtered and concentrated to afford the crude product. This was chromatographed on silica gel using 35%-45% ethyl acetate/hexane to yield 5.3 g of pure 3-[(4-methoxyphenyl)sulfonyl]-4-phenylbutan-1-ol, m/z=327 (M+Li).

Provenance & Evidence