[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone → HCID 178441050, compound

HRID 626195Notes

Reaction equation

HRID 626195 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][CH:3]=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[CH:4]=[CH:3][C:2]([OH:1])=[N:7][CH:6]=2)/[CH2:9][CH3:10])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanoneHCID 178458546HCID 178458546, compound

Product 1

HCID 178441050HCID 178441050, compound

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, 1-(6-hydroxypyridin-3-yl)propan-1-one (0.3 g, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (1.37 g, 2.5 eq) to give the desired Z-product (Z and E isomer can be separated via column chromatography).

Workup

  1. customgeneral procedure of McMurry reaction
  2. customto give the desired
  3. customZ-product (Z and E isomer can be separated via column chromatography)

Sources & evidence

ORD record
ord-b6d61682dbc64fc182da9b954492794f
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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