1-(2,3-Dihydro-1-benzofuran-5-yl)propan-1-one → 4-(1-(6-Chloropyridin-3-yl)-2-(2,3-dihydrobenzofuran-5-yl)but-1-enyl)phenol

HRID 626257Notes

Reaction equation

HRID 626257 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH2:11][CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Cl:14][C:15]1[N:20]=[CH:19][C:18]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29]C3CCCCO3)=[CH:25][CH:24]=2)=O)=[CH:17][CH:16]=1>>[Cl:14][C:15]1[N:20]=[CH:19][C:18]([C:21]([C:23]2[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=2)=[C:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)[CH2:11][CH3:12])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 40673881-(2,3-Dihydro-1-benzofuran-5-yl)propan-1-oneHCID 89655790(6-chloropyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

Product 1

HCID 1235660194-(1-(6-Chloropyridin-3-yl)-2-(2,3-dihydrobenzofuran-5-yl)but-1-enyl)phenolYield 37%

Procedure

According to general procedure of McMurry reaction as example 1, step D described, 1-(2,3-dihydrobenzofuran-5-yl)propan-1-one (610 mg, 1.1 eq) was reacted with (6-chloropyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone (1.0 g, 1.0 eq) to give 440 mg desired product (37%, Z/E=1/1).

Workup

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

Sources & evidence

ORD record
ord-39d3d5bdc9d94a8b8ebc991cead30689
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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