[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone → 4-(1-(4-(2-chloroethoxy)phenyl)-1-(4-hydroxyphenyl)-but-1-en-2-yl)-1-methylpyridin-2(1H)-one

HRID 626189Notes

Reaction equation

HRID 626189 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][C:3]1=[O:12].[Cl:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=O)=[CH:19][CH:18]=1>>[Cl:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:8]([C:5]2[CH:6]=[CH:7][N:2]([CH3:1])[C:3](=[O:12])[CH:4]=2)[CH2:9][CH3:10])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanoneHCID 896573541-methyl-4-propionylpyridin-2(1H)-one

Product 1

HCID 1212666934-(1-(4-(2-chloroethoxy)phenyl)-1-(4-hydroxyphenyl)-but-1-en-2-yl)-1-methylpyridin-2(1H)-one

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, 1-methyl-4-propionylpyridin-2(1H)-one (105 mg, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (352 mg, 2.0 eq) to give the desired product (Z/E=1:1).

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-e0357f171b434d5caa0183019576ef17
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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