HCID 12379536, compound → HCID 78135063, compound

HRID 626224Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)=O.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][NH:33][CH3:34])=[CH:26][CH:25]=2)=O)=[CH:18][CH:17]=1>>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)=[C:22]([C:19]1[CH:18]=[CH:17][C:16]([OH:15])=[CH:21][CH:20]=1)[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][NH:33][CH3:34])=[CH:26][CH:25]=1

Participants

Reactant 2

HCID 12379536HCID 12379536, compound

HCID 89656018HCID 89656018, compound

Product 1

HCID 78135063HCID 78135063, compoundYield 85%

Procedure

According to general procedure of McMurry reaction as example 1, step D described, 3-chloro-1-(2,3-dihydrobenzofuran-5-yl)propan-1-one (0.85 g, 1.0 eq) was reacted with (4-hydroxyphenyl)(4-(2-(methylamino)ethoxy)phenyl)methanone (1.0 g, 1.0 eq) to give 1.2 g desired product (85%, Z/E=1/1). 1H NMR (400 MHz, DMSO-d6) δ 9.87 (s, 1H), 7.02-7.54 (m, 6H), 6.70-6.84 (m, 5H), 4.22 (t, J=8.4 Hz, 2H), 4.03 (t, J=6.0 Hz, 2H), 3.48 (t, J=5.6 Hz, 2H), 2.89-3.05 (m, 4H), 2.42 (s, 3H), 2.13 (t, J=8.4 Hz, 2H); m/z=450[M+1]+.

Workup

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

Sources & evidence

ORD record: ord-bd5697d5485a4823a4e04cfb7e4507a3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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