Methanol → 5-(Hydroxymethyl)morpholin-3-one

Participants

Reaction Steps

Sodium tert-butoxide (6.70 g, 59.7 mmol) was dissolved in tert-amyl alcohol (40 mL). To this, a tert-amyl alcohol solution (90 mL) of 2-chloro-N-(2-hydroxy-1-hydroxymethylethyl)acetamide (4.00 g, 23.9 mmol) was added dropwise at room temperature over 30 minutes, and the mixture was stirred at room temperature for 2 hours. To this, methanol (25 mL) and water (1.5 mL) were successively added and the mixture was further stirred at room temperature for 30 minutes. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=80/20) to give 5-(hydroxymethyl)morpholin-3-one (Compound EE) (2.00 g, yield: 64%).

Provenance & Evidence