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

HRID 1732437
Notes
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Reaction equation

HRID 1732437 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 44562749HCID 44562749, compound

Product 1

HCID 100595943-Methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperatureThe reaction mixture is thereafter cooled to room temperature
  2. concentrationconcentrated at reduced pressure
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes