Methyl iodide → 3-{3-[3-(4-Acetyl-3-methoxy-2-propylphenoxy)-propoxy]-2-pyridyl}-propionic acid methyl ester

HRID 55261Notes

Reaction equation

HRID 55261 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[C:19]([OH:26])[C:18]=2[CH2:27][CH2:28][CH3:29])=[CH:10][CH:9]=[CH:8][N:7]=1.[C:31](=O)([O-])[O-].[Cs+].[Cs+].IC>>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[C:19]([O:26][CH3:31])[C:18]=2[CH2:27][CH2:28][CH3:29])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 545204963-{3-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)-propoxy]-2-pyridyl}-propionic acid methyl ester

Product 1

HCID 543019843-{3-[3-(4-Acetyl-3-methoxy-2-propylphenoxy)-propoxy]-2-pyridyl}-propionic acid methyl esterYield 91.9%

Procedure

Under the conditions of example 2 A, 600 mg of 3-{3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propoxy]-2-pyridyl}-propionic acid methyl ester in the presence of 940 mg of cesium carbonate instead of potassium carbonate is reacted with 205 mg of iodomethane, worked up, and the crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate. 570 mg of 3-{3-[3-(4-acetyl-3-methoxy-2-propylphenoxy)-propoxy]-2-pyridyl}-propionic acid methyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate

Sources & evidence

ORD record
ord-6418b49c36394e6e902886b5499d3266
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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