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

HRID 1251412노트

반응식

HRID 1251412 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-11feedd4632945dba16462f10905a27d
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06342508B1

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