Methyl 3,3-dimethoxycyclobutane-1-carboxylate → (3,3-Dimethoxycyclobutyl)methanol

Participants

Reaction Steps

To a stirring solution of 3,3-dimethoxy-cyclobutanecarboxylic acid methyl ester, (J. Org. Chem. 1988, 53, 3841 and J. Org. Chem. 1996, 61, 2174) (15.0 g, 86.1 mmol) in 40 mL of tetrahydrofuran at 0° C. (ice/water bath) was added dropwise a solution of lithium aluminum hydride (103.3 mL, 1M tetrahydrofuran). After the addition was complete the reaction was warmed to room temperature and stirred 12 hours. The reaction was worked-up using the method of Feiser and Feiser, and then filtered through a plug of Celite and concentrated under reduced pressure to yield (3,3-dimethoxy-cyclobutyl)-methanol (12.4 g, 99% crude yield) as a colorless oil. This material was used without further purification.

Provenance & Evidence