[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone → 4-(2-(Benzo[d]oxazol-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

HRID 626220Notes

Reaction equation

HRID 626220 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH2:11][CH3:12])=[CH:9][C:4]=2[N:3]=[CH:2]1.[Cl:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=O)=[CH:20][CH:19]=1>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH2:11][CH3:12])=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[C:21]3[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][Cl:14])=[CH:19][CH:20]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanoneHCID 1190847101-(5-Benzoxazolyl)-1-propanone

Product 1

HCID 1239169244-(2-(Benzo[d]oxazol-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenolYield 16%

Procedure

According to general procedure of McMurry reaction as example 1, step D described, 1-(benzo[d]oxazol-5-yl)propan-1-one (0.6 g, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (1.42 g, 1.5 eq) to give 0.23 g desired product (15%, Z/E=1/1) as a white solid.

Workup

  1. customAccording to general procedure of McMurry reaction as example 1, step D

Sources & evidence

ORD record
ord-d92112ab275141fa9530fd3d1f8a78f4
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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