3-(Chloromethyl)pyridine hydrochloride → 2-(4-Methoxy-benzensulfonyl)-2-methyl-3-pyridin-3-yl-propionic acid ethyl ester

HRID 565319ノート

反応式

HRID 565319 の反応式
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([S:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:6])[CH3:2].Cl.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26]Cl)[CH:21]=1>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C(Cl)Cl.[OH-].[Na+]>[CH2:1]([O:3][C:4](=[O:18])[C:5]([S:7]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)(=[O:8])=[O:9])([CH3:6])[CH2:26][C:22]1[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=1)[CH3:2]

参加物

6

反応物 2

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 206605032-(4-Methoxy-benzenesulfonyl)propionic acid ethyl ester

生成物 1

HCID 110466942-(4-Methoxy-benzensulfonyl)-2-methyl-3-pyridin-3-yl-propionic acid ethyl ester

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a stirred solution of 2-(4-methoxy-benzenesulfonyl)propionic acid ethyl ester (2.7 gm, 10 mmol), 3-picolyl chloride hydrochloride (3.2 g, 20 mmol). and triethyl benzylammonium chloride (1 g) in methylene chloride (400 ml), 10 N NaOH (30 ml) was added. The reaction was continued at room temp for 48 hours. At the end, the organic layer was separated and washed well with water. The organic layer was dried, filtered and concentrated. The crude product obtained was purified by silica-gel column chromatography. The column was eluted with 50% ethyl acetate: hexane. 2-(4-Methoxy-benzensulfonyl)-2-methyl-3-pyridin-3-yl-propionic acid ethyl ester was isolated as brown oil. Yield 3.0 g, 82%; Brown oil; MS: 364 (M+H)+.

後処理

  1. customAt the end, the organic layer was separated
  2. washwashed well with water
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customwas purified by silica-gel column chromatography
  8. washThe column was eluted with 50% ethyl acetate

出典と根拠

ORDレコード
ord-1ec644bec65644d3a5444cfffb9e8aba
出典データセット
uspto-grants-2001_01
特許番号
US06172057B2

反応ノート

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