Sodium hydride → 2-(2,2-Diethoxyethoxy)-1,1-dimethoxyethane

Participants

Reaction Steps

To a solution of glycolaldehyde dimethyl acetal (25 g, 236 mmol) in 750 mL of THF at 0° C. was added portionwise 14.1 g (353 mmol) of a 60% suspension of NaH in oil. The solution was warmed to room temperature, and then to 60° C. overnight. After cooling to room temperature, and then to 0° C., 69.9 g (353 mmol) of bromoacetaldehyde diethyl acetal in 200 mL of THF was added dropwise over 30 minutes. The reaction was warmed to room temperature, and then to reflux for 2 days. The reaction was cooled to room temperature, filtered through a pad of celite, and concentrated by rotary evaporation while keeping the bath temperature below 40° C. The residue was purified by column chromatography on silica gel (0 to 30% EtOAc in hexanes) to provide C-1 as a yellow oil. Data for C-1:1 H NMR (CDCl3, 500 MHz) δ 4.65 (m, 1H), 4.5 (m, 1H), 3.7 (m, 2H), 3.55 (m, 6H), 3.4 (s, 6H), 1.2 (M, 6H) ppm.

Provenance & Evidence