Acetic Acid → 3-Methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

反応式

[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH:10]([CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15])[C:9](=[O:16])[CH:8]=[CH:7]1)=[O:4].[BH4-].[Na+].C(O)(=O)C>CO>[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]([OH:16])[CH:10]1[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15])=[O:4]

参加物

反応条件

温度: 80 °C

実験手順

A 180 mg quantity of 4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone and 90 mg of sodium borohydride are dissolved in 20 ml of methanol, and the solution is refluxed at 80° C. for one hour. The reaction mixture is thereafter cooled to room temperature, and 20 ml of acetic acid is added to the mixture. The resulting mixture is stirred for 30 minutes and then concentrated at reduced pressure. The concentrate is distilled in a vacuum, giving 3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol (compound (3), R2 =CH3) in a yield of 94%, b.p. 63°-67° C./0.01 mm Hg.