[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone → 6-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)but-en-2-yl)pyridin-3-ol

HRID 626199Notes

Reaction equation

HRID 626199 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=O)[CH2:9][CH3:10])=[N:6][CH:7]=1.[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=O)=[CH:18][CH:17]=1>>[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:8]([C:5]2[N:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[CH2:9][CH3:10])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanoneHCID 1125838461-(5-Hydroxypyridin-2-yl)propan-1-one

Product 1

HCID 1371468096-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)but-en-2-yl)pyridin-3-ol

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, 1-(5-hydroxypyridin-2-yl)propan-1-one (0.15 g, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (0.549 g, 2.0 eq) to give the desired product (Z/E=1/1).

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-942ed8b2886748848a8baf6839d88361
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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