1-Phenyl-1-propanone → 6-(1-(4-(2-(Methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)pyridin-3-ol

HRID 626160Notes

Reaction equation

HRID 626160 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:27]=[CH:26][C:13]([O:14][CH2:15][CH2:16][N:17]([CH3:25])C(=O)OC(C)(C)C)=[CH:12][CH:11]=2)=O)=[N:6][CH:7]=1.[C:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)[CH2:29][CH3:30]>>[CH3:25][NH:17][CH2:16][CH2:15][O:14][C:13]1[CH:12]=[CH:11][C:10]([C:8]([C:5]2[N:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:29][CH3:30])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 89656144Tert-butyl 2-(4-(5-hydroxypicolinoyl)phenoxy)ethyl(methyl)carbamate

Product 1

HCID 781355046-(1-(4-(2-(Methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)pyridin-3-ol

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, tert-butyl 2-(4-(5-hydroxypicolinoyl)phenoxy)ethyl(methyl)carbamate (1.0 eq) was reacted with propiophenone (3.0 eq) to give the desired product (Z/E=1/1). m/z=375[M+1]+.

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-d3b9bdc8fd074551981cad151c0f9b7c
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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