Sodium Hydroxide → HCID 54154673, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl (2R,3R)-2-(3-trimethylsilyl-2-propyne-1-yl)-3-hydroxybutanoate (5.6 g, 24.56 mmol) in THF-methanol (3:1, 160 mL) is added 2 M aqueous sodium hydroxide solution (40 mL, 36.8 mmol). The solution is stirred at 23° C. for 20 h, then concentrated and extracted with hexanes (100 mL). The aqueous layer is acidified to pH 3 with 1 M HCl and is extracted with two 100 mL portions of EtOAc. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (2R,3R)-2-(2-propyne-1-yl)-3-hydroxybutanoic acid as an oil (3.0 g, 86% yield).

Provenance & Evidence