Tetrahydrofuran → 2-Chloroethanol

Participants

Reaction Steps

A two neck Kjeldahl flask of 50 ml into which a stirrer was put was charged with 2.15 g (10 mmol) of 1-adamantylmethyl chloromethyl ether obtained in (1), 0.97 g (12 mmol) of 2-chloroethanol, 1.52 g (15 mmol) of triethylamine and dried THF, and it was equipped with a coiled condenser to reflux and stir the solution for 8 hours. Triethylamine hydrochloride was filtered, and gas chromatographic analysis was carried out to find that chloroethyl chloromethyl ether was completely converted and that 2.25 g (8.7 mmol, isolation yield: 86.9%) of a colorless liquid which was the intended product was obtained at a selectivity of 98.5%.

Provenance & Evidence