4-Pentyn-1-ol → 3-[3-Hydroxy-6-(5-hydroxy-1-pentynyl)-2-pyridyl]-propionic acid methyl ester

HRID 55313

Reaction equation

HRID 55313 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.[CH2:15]([OH:20])[CH2:16][CH2:17][C:18]#[CH:19]>>[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]([C:19]#[C:18][CH2:17][CH2:16][CH2:15][OH:20])[N:7]=1

Participants

3

Reactant 2

HCID 793464-Pentyn-1-olHCID 544750193-(3-Hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester

Product 1

HCID 543978793-[3-Hydroxy-6-(5-hydroxy-1-pentynyl)-2-pyridyl]-propionic acid methyl esterYield 28%

Procedure

Under the conditions of example 5 A, 5 g of 3-(3-hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester is reacted with 1.37 g of 4-pentyn-1-ol, worked up, and the crude product is chromatographed on silica gel with hexane/0-4% methanol. 1.2 g of 3-[3-hydroxy-6-(5-hydroxy-1-pentynyl)-2-pyridyl]-propionic acid methyl ester is obtained as colorless oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-4% methanol

Sources & evidence

ORD record
ord-3041615f29b8409b826be1c81f949e26
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Linked notes

Loading…