2,3-Dihydroxybutanedioic Acid → 2-Ethyl-2-thiophen-2-yl-butan-1-ol

Participants

Reaction Steps

A solution of 2-methyl-2-thiophen-2-yl-propionic acid methyl ester (3.66 g, 17.2 mmol) in CH2Cl2 (85 mL) at 0° C. is treated with diisobutylaluminum hydrde (Dibal-H, 1.0 M PhMe, 38.0 mL, 384.0 mmol) and warmed to rt overnight. The reaction mixture is carefully poured into 1N tartaric acid (100 mL) and stirred for 3 d. The layers are separated and the aqueous layer is extracted with CH2Cl2 (100 mL). The combined extracts are dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% to 75% EtOAc to give 2-ethyl-2-thiophen-2-yl-butan-1-ol (2.87 g, 90%) as a pink oil.

Provenance & Evidence