Lithium hydroxide, monohydrate → HCID 53959927, compound

Participants

Reaction Steps

A solution of methyl (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxyhexanoate (6.5 g, 31.9 mmol) in 100 mL of water—MeOH—THF (1:1:4) is treated with lithium hydroxide monohydrate (1.6 g, 38 mmol) and stirred overnight. The reaction mixture is acidified to pH 2 using 1 M aqueous sodium hydrogen sulfate and extracted with two 100-mL portions of EtOAc. The combined organic layers are washed with two 25-mL portions of saturated aqueous sodium chloride, dried over sodium sulfate and filtered, and the solvents are removed under reduced pressure. Purification by flash chromatography on silica gel eluting with 10% EtOAc-hexanes affords 6.0 g (100%) of (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxyhexanoic acid as a gum.

Provenance & Evidence