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

HRID 565319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 565319
[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]

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1ec644bec65644d3a5444cfffb9e8aba
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172057B2

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