Acetic Acid → 3-Methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanol

HRID 261634Notes

Reaction equation

HRID 261634 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH:10]([CH2:11][C:12]#[C: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][C:12]#[C:13][CH2:14][CH3:15])=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 20394599HCID 20394599, compound

Product 1

HCID 203946003-Methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (890 mg) and 350 mg of sodium borohydride are dissolved in 20 ml of methanol, and the mixture is refluxed at 80° C. for one hour. On completion of the reaction, the mixture is cooled to room temperature. With addition of 60 ml of acetic acid, the mixture is stirred for 30 minutes and thereafter concentrated in a vacuum. The residue is purified with a silica gel column and distilled in a vacuum, affording 3-methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanol (compound (1), R2 =CH3) in a yield of 94%, b.p. 65°-69° C./0.15 mm Hg.

Workup

  1. customOn completion of the reaction
  2. temperaturethe mixture is cooled to room temperature
  3. concentrationconcentrated in a vacuum
  4. customThe residue is purified with a silica gel column
  5. distillationdistilled in a vacuum

Sources & evidence

ORD record
ord-279fb28cf4a64ff1a97723e0452e924c
Source dataset
uspto-grants-1979_08
Patent number
US04166188

Reaction notes

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