Benzyl Bromide → HCID 19366841, compound

Participants

Reaction Steps

Part A: To a solution of 4.0 g (15 mmol) of 3-[(4-butoxyphenyl)sulfonyl]propan-1-ol from Example 26 and 6 mL of DMPU in 100 mL of anhydrous THF at -70 C under nitrogen, was added 3.9 mL (1.9 g, 29 mmol) of a 10.0 M solution of n-butyllithium in hexane. After stirring for 30 min. at -70 C., 1.6 mL (2.3 g, 13 mmole) of benzyl bromide was added. After 15 hours, the reaction mixture was cooled to zero C. and 25 mL of saturated ammonium chloride solution was added. Ethyl acetate and water were added, 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 8.4 g of crude product. This was chromatographed on silica gel using 25%-35% ethyl acetate/hexane to yield 4.3 g of pure 3-[(4-butoxyphenyl)sulfonyl]-4-phenylbutan-1-ol.

Provenance & Evidence