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

HRID 1732437Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

temperatureThe reaction mixture is thereafter cooled to room temperature
concentrationconcentrated at reduced pressure
distillationThe concentrate is distilled in a vacuum

Sources & evidence

ORD record: ord-cfd05e9924f7488d9354257a5b5b1640
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04237308

Reaction notes

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