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

HRID 991065Notes

Reaction equation

HRID 991065 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

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), 10N 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)+.

Workup

  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

Sources & evidence

ORD record
ord-18ee37c734104b71bc982a9f21d357b8
Source dataset
uspto-grants-2002_10
Patent number
US06462073B2

Reaction notes

Loading…