Diethyl Ether → HCID 57999483, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 63 (0.118 g, 1.5 mmol), in dry THF (5 mL), at −78° C., under a nitrogen atmosphere, was added n-BuLi (0.6 mL, 1.5 mmol, using a 2.5M solution in hexane) dropwise. Stirring continued for 10 min at −78° C. and then MgBr2.Et2O (0.4 g, 1.5 mmol) was added. The resulting mixture was warmed to −45° C. over a 2 hours period, and then it was cooled back to −78° C., and a solution of 76 (0.081 g, 0.28 mmol) in dry THF (5 mL) was added dropwise. Following the addition, the reaction mixture was warmed to −45° C. over a 2 hours period and then diluted with aqueous NH4Cl solution (5 mL) and AcOEt (20 mL). The resulting mixture was gradually warmed to room temperature, the organic phase was separated and the aqueous phase extracted with AcOEt. The combined organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (75% ethyl acetate-hexane) to give 77 (0.052 g, 50% yield) as a colorless viscous liquid.

Provenance & Evidence