4-Chlorobenzyl alcohol → HCID 19831107, compound

HRID 1493231Notes

Reaction equation

HRID 1493231 reaction equation
ClC1C=NC=CC=1C#N.ClC1C=CC(CO)=CC=1.[H-].[Na+].C([Li])CCC.[Cl:26][C:27]1[CH:46]=[CH:45][C:30]([CH2:31][O:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][C:38]=2[C:39](=[O:44])[CH2:40][CH2:41][CH2:42][CH3:43])=[CH:29][CH:28]=1.B.[Na]>CN(C)C=O.ClC1C=CC(COC2C=NC=CC=2C#N)=CC=1.C(OCC)C>[Cl:26][C:27]1[CH:46]=[CH:45][C:30]([CH2:31][O:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][C:38]=2[CH:39]([OH:44])[CH2:40][CH2:41][CH2:42][CH3:43])=[CH:29][CH:28]=1

Participants

10

Reactant 6

HCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydrideHCID 106783063-Chloropyridine-4-carbonitrileHCID 19831108HCID 19831108, compoundHCID 178418339ButyllithiumHCID 178418435HCID 178418435, compound

Product 1

HCID 19831107HCID 19831107, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 54007594HCID 54007594, compoundSolvent

Procedure

Starting from 3-chloro-4-pyridine carbonitrile, by reaction with 4-chlorobenzyl alcohol in the presence of sodium hydride in dimethylformamide, 3-(4-chlorobenzyloxy)-4-pyridine carbonitrile is obtained, which is reacted with butyllithium in diethyl ether to 3-(4-chlorobenzyloxy)-4-valeryl pyridine. The keto group of this 4-valeryl derivative is reduced with sodium boron hydride to the hydroxyl group; 1-[3-(4-chlorobenzyloxy)-4-pyridyl]-1-pentanol is obtained. The hydroxyl group of the pentanol derivative is exchanged with thionyl chloride in methylene chloride for a chlorine group, 3-(4-chlorobenzyloxy)-4-(1-chloropentyl)-pyridine is obtained. By subsequent reaction with imidazole in the presence of sodium hydride (analogously to example 13), the 3-(4-chlorobenzyloxy)-4-[1-(1-imidazolyl)-pentyl]-pyridine is obtained.

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-aac63efba5434fbebe7a25331abe6e95
Source dataset
uspto-grants-1991_06
Patent number
US05021434

Reaction notes

Loading…