1-Phenyl-1-propanone → 4-(2-Phenyl-1-(6-(3-(pyrrolidin-1-yl)propyl)pyridin-3-yl)but-1-enyl)phenol

HRID 626166Notes

Reaction equation

HRID 626166 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C4CCCCO4)=[CH:19][CH:18]=3)=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=O)[CH2:31][CH3:32]>>[C:34]1([C:30]([CH2:31][CH3:32])=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[C:12]2[CH:13]=[N:14][C:9]([CH2:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:10][CH:11]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 89672867(6-(3-(pyrrolidin-1-yl)propyl)pyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yl-oxy)phenyl)methanone

Product 1

HCID 896572744-(2-Phenyl-1-(6-(3-(pyrrolidin-1-yl)propyl)pyridin-3-yl)but-1-enyl)phenolYield 18%

Procedure

Following the general procedure of McMurry reaction as described in example 1, step B, (6-(3-(pyrrolidin-1-yl)propyl)pyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yl-oxy)phenyl)methanone (1.0 g, 2.5 mmol) was reacted with propiophenone (1.0 g, 7.6 mmol) to give 186 mg desired product (17.8% yield, Z/E=3/1). m/z=413[M+1]+.

Workup

  1. customthe general procedure of McMurry reaction

Sources & evidence

ORD record
ord-f9f17e77952a4754b383ed18d4aa0469
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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