Acetyl chloride → HCID 12347356, compound

Participants

Reaction Steps

(Tetrahedron, (1977), 33, 1113) A solution of 3-oxocyclopentanecarboxylic acid (10.013 g, 78 mmol) and trimethyl orthoformate (60.5 mL, 547 mmol) in MeOH (120 mL) was treated with acetyl chloride (7.78 mL, 109 mmol) and stirred under a nitrogen atmosphere for 5 days. The reaction solution was poured into a stirred suspension of anhydrous sodium carbonate (32 g) in pentane (250 mL) and stirred for 3 hrs. The solids were removed by filtration (2×) and concentrated under reduced pressure to give the target compound (15.4 g, 82 mmol, 105% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.67 (3 H, s), 3.20 (3 H, s), 3.18 (3 H, s), 2.82-2.93 (1 H, m), 2.01-2.15 (2 H, m), 1.77-2.01 (4 H, m).

Provenance & Evidence