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

HRID 261634ノート

反応式

HRID 261634 の反応式
[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]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 20394599HCID 20394599、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-279fb28cf4a64ff1a97723e0452e924c
出典データセット
uspto-grants-1979_08
特許番号
US04166188

反応ノート

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