Ethyl Acetate → (3,3-Dimethoxycyclobutyl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 3,3-dimethoxy-cyclobutanecarboxylic acid methyl ester (1.48 g, 8.49 mmol) in tetrahydrofuran (5 ml) was added dropwise to a cooled 0° C. suspension of lithium aluminum hydride (0.39 g, 10.19 mmol) in tetrahydrofuran (15 ml). The reaction was allowed to warm to 25° C. and stirred for 17 h. After such time, ethyl acetate (1 ml) and a few crystals of sodium sulphate decahydrate were added with caution and stirred until gas evolution stopped. The resulting residue was filtered through a short celite pad and washed with ethyl acetate and then concentrated in vacuo to afford (3,3-dimethoxy-cyclobutyl)-methanol (1.04 g, 84%) as a light yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.57 (brs, 1H, OH), 1.82-1.97 (m, 2H, CH2), 2.23-2.36 (m, 3H, CH2 and CH), 3.14 (s, 3H, OCH3), 3.16 (s, 3H, OCH3), 3.64-3.68 (m, 2H, OCH2).

Provenance & Evidence