HCID 12347356, compound → HCID 12347383, compound

Participants

Reaction Steps

A solution of methyl 3,3-dimethoxycyclopentanecarboxylate, methyl 3,3-dimethoxycyclopentanecarboxylate (14.68 g, 78 mmol), in THF (100 mL) was cooled (0° C. ice bath) and treated with 1.0N lithium aluminum hydride in THF (74.1 mL, 74.1 mmol) by dropwise addition. Upon completion of the addition, the reaction was warmed to room temperature and stirred for 6 hrs. The reaction was quenched by slow addition of Na2SO4-10H2O (17 g). The suspension was stirred for 1 hr, treated with anhyd. Na2SO4, and filtered. The filtrate was concentrated to afford the target compound (12.01 g, 75.0 mmol, 96% yield) as a colourless oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.54 (2 H, s), 3.20 (3 H, s), 3.19 (3 H, s), 2.21-2.32 (1 H, m), 1.99 (1H, dd, J=13.28, 9.00 Hz), 1.85-1.91 (1 H, m), 1.78-1.85 (2 H, m), 1.73-1.78 (1 H, m), 1.56 (1 H, dd, J=13.12, 7.32 Hz), 1.40-1.48 (1 H, m).

Provenance & Evidence