Ammonium Chloride → (1-Hydroxymethylcyclopropyl)acetic acid methyl ester

Participants

Reaction Steps

To a stirred solution of crude 5-oxa-spiro[2.4]heptan-6-one (2.24 g, ca. 20 mmol; prepared according to the method of EP 0 678 515 A1 (herein incorporated by reference in its entirety for all purposes): impurity is N,N-dimethyl acetamide) in anhydrous methanol (40 mL) in water bath, was added sodium methoxide (1.296 g, 24 mmol). After 15 min, ammonium chloride (2 g) was added and the mixture was stirred at room temperature for 30 min. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1)) to afford 5.8 g (47%) of (1-hydroxymethyl-cyclopropyl)-acetic acid methyl ester as a colorless oil. 1H-NMR (200 MHz, CDCl3) δ 0.47-0.61 (4H, m), 2.44 (2H, s), 2.55 (1H, t, J=5.6 Hz), 3.48 (2H, d, J=5.6 Hz), 3.69 (3H, s).

Provenance & Evidence