Methanol → Methyl 2,2-difluoro-4-hydroxybutanoate

Participants

Reaction Conditions

Reaction Steps

In a 4 L flask equipped with a reflux condenser and 1 L dropping funnel, a solution of BH3.Me2S complex (10M, 88 mL) in dry dicholoromethane (1 L) is slowly added over a 2 hour period to a stirred solution of the methyl 2,2-difluorosuccinate (120 g, 0.714 moles) in dry tetrahydrofuran at 20° C. After refluxing (bath temperature 80° C.) for about 15 hours, the mixture is allowed to cool to room temperature and methanol (1 L) is slowly added. Evaporation yields methyl 2,2-difluoro-4-hydroxybutyrate as an oil which is stripped with methanol (1 L) and finally with CCl4 to yield a yellow oil: 100 g (92%).

Provenance & Evidence