Water → 2-(Oxan-4-yloxy)acetic acid

Participants

Reaction Conditions

Reaction Steps

A solution of tetrahydro-2H-pyran-4-ol (286 μl, Acros) in tetrahydrofuran (4 ml) was added with sodium iodoacetate (624 mg), and successively added with sodium hydride (198 mg) as several portions at 0° C., and the mixture was stirred at the same temperature for 45 minutes, and then further stirred at room temperature for 23 hours. The reaction mixture was cooled again to 0° C., and then carefully added with water and then with chloroform, and the organic layer was separated. The aqueous layer was acidified (pH 4) with 1 N hydrochloric acid, and extracted three times with chloroform, and the combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure to obtain the title compound (43.4 mg).

Provenance & Evidence