[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone → (Z)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(1,4-dioxaspiro[4.5]decan-8-yl)but-1-enyl)phenol

HRID 626181Notes

Reaction equation

HRID 626181 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11](=O)[CH2:12][CH3:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]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: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)=[C:11](\[CH:8]2[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]2)/[CH2:12][CH3:13])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanoneHCID 896574821-(1,4-Dioxaspiro[4.5]decan-8-yl)propan-1-one

Product 1

HCID 89657460(Z)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(1,4-dioxaspiro[4.5]decan-8-yl)but-1-enyl)phenolYield 16%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, 1-(1,4-dioxaspiro[4.5]decan-8-yl)propan-1-one (259 mg, 1.3 mmol) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (360 mg, 1.3 mmol) to give 90 mg title compound (Z-isomer, 16% yield) and 110 mg E-isomer (19% yield) as well.

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-688f09a1891e465dbeb585839af96477
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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