1-Phenyl-1-propanone → HCID 121266696, compound

HRID 626115Notes

Reaction equation

HRID 626115 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)[CH2:2][CH3:3].[Br:11][C:12]1[CH:13]=[C:14]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=O)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][Br:21]>>[Br:11][C:12]1[CH:13]=[C:14]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:1]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:2][CH3:3])[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][Br:21]

Participants

3

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 89656372HCID 89656372, compound

Product 1

HCID 121266696HCID 121266696, compoundYield 36%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, propiophenone (0.2 g, 3.0 eq) was reacted with (3-bromo-4-(2-bromoethoxy) phenyl)(4-hydroxyphenyl)methanone (0.2 g, 1.0 eq) to give 0.09 g desired product (36% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.42 (s, 1H), 7.01-7.0 (m, 7H), 6.87 (d, J=8.4 Hz, 1H), 6.82 (d, J=8.4 Hz, 1H), 6.71 (d, J=8.4 Hz, 1H), 6.48 (d, J=8.4 Hz, 1H), 4.36 (t, J=6.8 Hz, 1H), 4.19 (t, J=6.4 Hz, 1H), 3.70 (t, J=6.4 Hz, 1H), 3.59 (t, J=6.8 Hz, 1H), 2.46 (q, J=6.4 Hz, 2H), 0.92 (t, J=6.0 Hz, 3H)

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-516be3909d9c42a891cdf220ba0d0c50
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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