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

HRID 261634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 261634
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-279fb28cf4a64ff1a97723e0452e924c
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04166188

Notizen zur Reaktion

Wird geladen…