Cyclohexanecarboxaldehyde → 4-(1-Formyl-cyclohexyl)-but-2-enoic acid methyl ester

HRID 2070553

反応式

HRID 2070553 の反応式
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][O:10][C:11](=[O:16])[CH:12](O)[CH:13]=[CH2:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:9][O:10][C:11](=[O:16])[CH:12]=[CH:13][CH2:14][C:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 16275CyclohexanecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 545123Methyl 2-hydroxybut-3-enoate

生成物 1

HCID 727655614-(1-Formyl-cyclohexyl)-but-2-enoic acid methyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of cyclohexanecarbaldehyde (6.3 mL) and 2-hydroxy-3-butenoic acid methyl ester (5 mL) in toluene (40 mL) was added para-toluenesulfonic acid monohydrate (20 mg), and the reaction mixture was heated under reflux by using a Dean-Stark apparatus for 16.5 hours. After cooling down to room temperature, the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=50:1 to 10:1) to give 4-(1-formyl-cyclohexyl)-but-2-enoic acid methyl ester (3.7 g).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux
  3. customfor 16.5 hours
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=50:1 to 10:1)

出典と根拠

ORDレコード
ord-0e9cb1be9eef4ba38d47d16c36ec66cc
出典データセット
uspto-grants-2012_10
特許番号
US08299296B2

関連ノート

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