Tetrahydrofuran → Acetic acid 2-(2-{2-[2-(2,2-dimethoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethyl ester

Participants

Reaction Steps

To a stirring suspension of sodium hydride (248 mg, 5.15 mmol in mineral oil) in THF (5 ml) was added through a syringe a solution of 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethanol (Compound 2) (1.0 g, 5.15 mmol) in THF (5 ml) at ambient temperature. After gas evolution had ceased, the mixture was stirred for 45 minutes at room temperature by which time a clear slightly yellow solution was obtained. Bromoacetaldehyde (8.71 g, 51.5 mmol) was added via syringe and the mixture stirred for 24 hours. Then ethyl acetate was (3 ml) was added and the mixture stirred at ambient temperature a further 2 hours. The mixture was poured into ether (100 ml) and extracted once each with 10% aqueous K2CO3 (30 ml) and brine (30 ml). The organic phase was dried (Na2SO4, filtered and evaporated. The residual oil was distilled to eliminate excess bromoacetaldehyde and the residual crude product was purified by flash chromatography using 100% ethyl acetate to afford the product (355 mg, 21%) as a colourless oil.

Provenance & Evidence