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

HRID 626253Notes

Reaction equation

[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH3:13])=[CH:7][C:5]=2[CH:6]=1.[Cl:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=O)=[CH:21][CH:20]=1>>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:12][CH3:13])=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[C:22]3[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][Cl:15])=[CH:20][CH:21]=3)=[CH:7][C:5]=2[CH:6]=1

Participants

Reactant 2

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

HCID 896729131-(2-Chlorobenzofuran-5-yl)propan-1-one

Product 1

HCID 1239950204-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenolYield 72.3%

Procedure

According to general procedure of McMurry reaction as example 1, step D described, 1-(2-chlorobenzofuran-5-yl)propan-1-one (140 mg, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (371 mg, 2.0 eq) to give 220 mg desired product (72%, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.23 (s, 1H), 7.21 (d, J=8.4 Hz, 1H), 7.16 & 7.10 (d, J=8.6 Hz, 2H), 7.00 & 6.99 (d, J=8.4 Hz, 1H), 6.90 & 6.81 (d, J=8.6 Hz, 2H), 6.76 & 6.70 (d, J=8.8 Hz, 2H), 6.52 & 6.44 (d, J=9.0 Hz, 2H), 6.45 (s, 1H), 4.73 & 4.48 (s, 1H), 4.26 & 4.08 (t, J=6.0 Hz, 2H), 3.83 & 3.72 (t, J=6.0 Hz, 2H), 2.50 (q, J=7.2 Hz, 2H), 0.91 (t, J=7.2 Hz, 3H).

Workup

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

Sources & evidence

ORD record: ord-eb74438f732c4707abfc2c7381528a21
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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