Water → HCID 67953936, compound

Participants

Reaction Steps

(R)-benzyl 3,3-difluorocyclopentanecarboxylate (13 g, 54.1 mmol) was dissolved in MeOH (200 mL) at room temperature with stirring then 0.5 M LiOH (216 mL, 108 mmol) was added. After stirring for 2 h, water was added to the reaction mixture and concentrated to remove volatile solvents. The aqueous layer was rinsed with Et2O (2×) then acidified to pH 3 with 1N HCl. The aqueous layer was extracted with methylene chloride (2×) and the organic layers were combined, dried (Na2SO4), and concentrated to give (R)-3,3-difluorocyclopentanecarboxylic acid (6.58 g, 43.8 mmol, 81% yield) as an oil. 1H NMR (MeOD3, 400 MHz) δ 3.03 (m, 1H), 2.33 (m, 2H), 1.95-2.20 (m, 4H); m/z=149.2 (M−H).

Provenance & Evidence