Methyl 4-pentynoate → 5-[3-Hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-4-pentynoic acid methyl ester

HRID 55310Notes

Reaction equation

HRID 55310 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8](I)[N:7]=1.[CH3:15][O:16][C:17](=[O:22])[CH2:18][CH2:19][C:20]#[CH:21]>>[CH3:15][O:16][C:17](=[O:22])[CH2:18][CH2:19][C:20]#[C:21][C:8]1[N:7]=[C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:14])[C:11]([OH:12])=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 543061Methyl 4-pentynoateHCID 544750193-(3-Hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester

Product 1

HCID 542841715-[3-Hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-4-pentynoic acid methyl esterYield 84.3%

Procedure

Under the conditions of example 5A, 2 g of 3-(3-hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester is reacted with 0.8 g of 4-pentynoic acid methyl ester, worked up, and the crude product is chromatographed on silica gel with hexane/0-30% ethyl acetate. 1.6 g of 5-[3-hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-4-pentynoic acid methyl ester of melting point 119°-121° C. is obtained.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-30% ethyl acetate

Sources & evidence

ORD record
ord-6f7f522312714d42969d4a45c59ccb43
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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