1-Phenyl-1-propanone → HCID 78135607, compound

HRID 626204Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)[CH2:2][CH3:3].[CH3:11][N:12]([CH3:32])[CH2:13][CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22](=O)[C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:18][C:17]1=[O:31]>>[CH3:11][N:12]([CH3:32])[CH2:13][CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[C:1]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:2][CH3:3])=[CH:18][C:17]1=[O:31]

Participants

Reactant 2

HCID 71481-Phenyl-1-propanone

HCID 89657436HCID 89657436, compound

Product 1

HCID 78135607HCID 78135607, compound

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, propiophenone (0.838 g, 3.0 eq) was reacted with 1-(3-(dimethylamino) propyl)-4-(4-hydroxybenzoyl)pyridin-2(1H)-one (0.8 g, 1.0 eq) to give the desired product (Z was prepared by preparative HPLC). 1H NMR (400 MHz, DMSO-d6) δ 9.54 (brs, 1H), 7.34 (d, J=6.8 Hz, 1H), 7.17-7.29 (m, 5H), 7.04 (d, J=8.4 Hz, 2H), 6.79 (d, J=8.4 Hz, 2H), 5.83 (d, J=1.6 Hz, 1H), 5.75 (dd, J=6.8 Hz, 1.6 Hz, 1H), 3.75 (t, J=6.8 Hz, 2H), 2.93 (t, J=6.8 Hz, 2H), 2.73 (s, 6H), 2.37 (q, J=7.2 Hz, 2H), 1.86-1.90 (m, 2H), 0.83 (t, J=7.2 Hz, 3H); m/z=403[M+1]+.

Workup

customgeneral procedure of McMurry reaction

Sources & evidence

ORD record: ord-0059d49d92d042c0b0b896d36e367cc9
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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