Methanol → HCID 67084471, compound

Participants

Reaction Steps

Add a solution of DIBAL (5.41 mL, 1.2 M in toluene, 6.48 mmol) dropwise over one h to a solution of (Z)-4-cyclopentyl-2-(5-methanesulfonyl-thiophen-2-yl)-but-2-enoic acid ethyl ester (939 mg, max. 2.59 mmol) in THF (5 mL) at to −78 ° C. Then allow the reaction mixture to warm slowly to r.t., and stir for 18 h. Add methanol (1.5 mL) at −78° C. and allow the reaction mixture to warm to r.t. Partition the residue between ethyl acetate (15 mL) and sodium potassium tartrate (15 mL). Then extract the aqueous layer with ethyl acetate. Combine the organic layers, wash them with saturated aqueous sodium chloride solution, dry over sodium sulfate and remove solvent under vacuum to give 812 mg crude product. MS (m/e): 323.0 (M+Na).

Provenance & Evidence