Ethyl Bromide → HCID 19366851, compound

Participants

Reaction Conditions

Reaction Steps

Part A: To a solution of 4.6 g (20 mmol) of 3-[(4-methoxyphenyl)sulfonyl]propane-1-ol from example 13 and 6 mL of DMPU in 60 mL of anhydrous THF at -70° C. under nitrogen, was added 5.8 mL (2.8 g, 44 mmol) of a 10.0 M solution of n-butyllithium in hexane. After stirring for 30 min. at -70° C., 1.6 mL (2.4 g, 22 mmole) of 1-bromoethane was added. After 2 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 4 g of crude product. This was chromatographed on silica gel using 40%-55% ethyl acetate/hexane to yield 2.4 g of pure 3-[(4-methoxyphenyl)sulfonyl]-pentan-1-ol, m/z=265 (M+Li).

Provenance & Evidence