Diethyl Ether → 2-Methoxyethoxymethyl ether

Participants

Reaction Steps

To 3.54 g (30 mmol) of 3-methyl-1,5-pentanediol in 30 ml of dry tetrahydrofuran (THF) at 0° was added 19.2 ml (30 mmol) of 1.56 M n-butyllithium. After 30 min, 3.74 g (30 mmol) of β-methoxyethoxymethyl chloride was added and the reaction was stirred overnight. The reaction was poured into ether and water. The aqueous phase was back-extracted twice with ether. Combined ether layers were washed with sat. NaCl solution and were dried over calcium sulfate. The crude product was placed on 1 m×20 cm prep. SiO2 plates which were then developed with 40% ethyl acetate/hexane. Removal of the second least polar band gave the monoether derivative of 3-methyl-1,5-pentanediol (II).

Provenance & Evidence