1-(5-Chlorothiophen-3-yl)propan-1-one → (E)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(5-chlorothiophen-3-yl)-but-1-enyl)phenol

HRID 626107Notes

Reaction equation

HRID 626107 reaction equation
[Cl:1][C:2]1[S:6][CH:5]=[C:4]([C:7](=O)[CH2:8][CH3:9])[CH:3]=1.[Cl:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=O)=[CH:17][CH:16]=1>>[Cl:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18](/[C:21](/[C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[C:7](/[C:4]2[CH:3]=[C:2]([Cl:1])[S:6][CH:5]=2)\[CH2:8][CH3:9])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 703834691-(5-Chlorothiophen-3-yl)propan-1-oneHCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

Product 1

HCID 89672888(E)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(5-chlorothiophen-3-yl)-but-1-enyl)phenolYield 45%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, 1-(5-chlorothiophen-3-yl)propan-1-one (1.5 g, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (2.0 g, 1.2 eq) to give 0.8 g desired product (45% yield, E).

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-3360b579eda74cbb9ee2440283fdd915
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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