Hydrochloric Acid → Methyl 4-(3-hydroxypropyl)benzoate

HRID 509898ノート

反応式

HRID 509898 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](O)=[O:13])=[CH:6][CH:5]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[BH4-].[Na+].Cl>C1COCC1.O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 227166883-(4-(Methoxycarbonyl)phenyl)propanoic acid

生成物 1

HCID 14425137Methyl 4-(3-hydroxypropyl)benzoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-(2-Carboxy-ethyl)-benzoic acid methyl ester (5 g, 24 mmol) is dissolved in THF (50 ml), N,N-carbonyldiimidazole (4.25 g, 26.2 mmol) is added and stirred for 1 h at room temperature. Then sodium borohydride (1.9 g, 50 mmol) and water (10 ml) are added to the reaction mixture and stirred for additional 1 h. 1M HCl is added dropwise to the reaction mixture, extracted with ethyl acetate, the organic phase is dried and concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol) to afford the title compound. LC (method F): tR=1.83 min; Mass spectrum (ESI+): m/z=195 [M+H]+.

後処理

  1. stirringstirred for additional 1 h
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is dried
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel (dichloromethane/methanol)

出典と根拠

ORDレコード
ord-987abdd8d26a4105b4c6ccf664ce0a4d
出典データセット
uspto-grants-2015_08
特許番号
US09096548B2

反応ノート

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