Ethyl Acetate → HCID 131725094, compound

Participants

Reaction Steps

n-Butyl lithium in hexane (1.6 M, 0.56 mL, 0.89 mmol) was added to a solution of triethylphosphono-3-methyl-2E-butenoate (264 mg, 1.0 mmol) in 5 mL of THF and 3 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) at −78° C. After stirring for 5 min, a solution of Intermediate 45 (15 mg, 0.20 mmol) in 1 mL of TF was added by cannulation. The resulting solution was stirred at −7° C. for 2 h and then quenched with saturated NH4Cl. The mixture was then extracted with diethyl ether (3×5 mL), washed with brine (1×10 mL), dried (Na2SO4) and concentrated to give a crude colorless oil. Purification by column chromatography using 5%. EtOAc in hexane afforded the title compound (20 mg, 85% yield) as a white solid:

Provenance & Evidence