1-Phenyl-1-propanone → 4-(1-(3-Fluoro-4-(3-(pyrrolidin-1-yl)prop-1-ynyl)phenyl)-2-phenylbut-1-enyl)phenol

HRID 626177Notes

Reaction equation

HRID 626177 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C3CCCCO3)=[CH:20][CH:19]=2)=O)[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[C:31]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=O)[CH2:32][CH3:33]>>[F:1][C:2]1[CH:3]=[C:4]([C:16]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)=[C:31]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:32][CH3:33])[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 89672877(3-fluoro-4-(3-(pyrrolidin-1-yl)prop-1-ynyl)phenyl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

Product 1

HCID 781357274-(1-(3-Fluoro-4-(3-(pyrrolidin-1-yl)prop-1-ynyl)phenyl)-2-phenylbut-1-enyl)phenolYield 35,868%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, (3-fluoro-4-(3-(pyrrolidin-1-yl)prop-1-ynyl)phenyl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone (155 mg, 0.38 mmol) was reacted with propiophenone (152 mg, 1.13 mmol) to give 58 g desired product (36% yield, Z/E=1/1). m/z=426[M+1]+.

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-14026de24d8c464f86e5181df09f34ff
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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