1-(Thiophen-3-yl)propan-1-one → 4-(1-(4-(2-Chloroethoxy)phenyl)-2-(thiophen-3-yl)but-1-enyl)phenol

HRID 626104Notes

Reaction equation

HRID 626104 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6](=O)[CH2:7][CH3:8])=[CH:2]1.[Cl:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=O)=[CH:16][CH:15]=1>>[Cl:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH2:7][CH3:8])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 5299441-(Thiophen-3-yl)propan-1-oneHCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

Product 1

HCID 1238962104-(1-(4-(2-Chloroethoxy)phenyl)-2-(thiophen-3-yl)but-1-enyl)phenolYield 95%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, 1-(thiophen-3-yl)propan-1-one (0.5 g, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (1.5 g, 1.5 eq) to give 1.3 g desired product (95% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.10-7.14 (m, 1H), 7.02-7.09 (m, 2H), 6.76-6.92 (m, 5H), 6.68-6.71 (m, 1H), 6.60-6.66 (m, 1H), 6.55-6.59 (m, 1H), 4.62 (s, 1H), 4.49 (s, 1H), 4.24 (t, J=6.0 Hz, 1H), 4.14 (t, J=6.0 Hz, 1H), 3.82 (t, J=6.0 Hz, 1H), 3.76 (t, J=6.0 Hz, 1H), 2.43-2.49 (m, 2H), 0.98 (t, J=7.6 Hz, 3H).

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-144eff3bc4a6424da9b0b14d42028f11
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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