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

HRID 261634노트

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HRID 261634 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-279fb28cf4a64ff1a97723e0452e924c
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04166188

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