Water → HCID 86208818, compound

Participants

Reaction Steps

Sodium hydride (4.44 g, 60% dispersion in oil, 111 mmol) was added to a solution of 1,4-butanediol (10.0 g, 111 mmol) in THF (200 mL). After stirring 1 h at rt, the mixture was cooled to 0° C. and methyl bromomethylacetate (10.82 mL, 114 mmol) was added and the reaction was allowed to warm to room temperature. After 16 h, water (100 mL) was added and the mixture was extracted with EtOAc (3×100 mL). The combined organic phase was washed with brine (2×100 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (20%→30% EtOAc/Hexane) to afford 2.88 g (16%) of (4-hydroxy-butoxy)-acetic acid methyl ester as a colorless oil.

Provenance & Evidence