Dimethyl dicarbonate → rel-Methyl (1R,2S)-3-oxo-2-pentylcyclopentaneacetate

Participants

Reaction Steps

104 Mg (0.49 mmole) of (+)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid (97:3 cis/trans ratio) in 0.5 ml of methanol were treated with 76 μl of dimethyl dicarbonate [CH3O(CO)O(CO)OCH3, origin: Bayer; 96 mg, 0.72 mmole, 1.5 eq.]. The resulting solution was heated to 45° during 16 h and then evaporated under vacuum. After distillation of the residue in a bulb-to-bulb apparatus (oven t. 150°/10 Pa), there were obtained 100 mg (0.44 mmole, yield 90%) of pure methyl (±)cis-3-oxo-2-pentyl-1-cyclopentaneacetate (97:3 cis/trans ratio).

Provenance & Evidence