1-(1-methyl-1H-benzo[d]imidazol-5-yl)propan-1-one → (Z)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(1-methyl-1H-benzo[d]-imidazol-5-yl)but-1-enyl)phenol

HRID 626244Notes

Reaction equation

HRID 626244 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](=O)[CH2:12][CH3:13])=[CH:10][C:5]=2[N:4]=[CH:3]1.[Cl:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=O)=[CH:21][CH:20]=1>>[Cl:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22](/[C:25](/[C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[C:11](\[C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[CH:3]=[N:4][C:5]=3[CH:10]=2)/[CH2:12][CH3:13])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 391039641-(1-methyl-1H-benzo[d]imidazol-5-yl)propan-1-oneHCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

Product 1

HCID 89672895(Z)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(1-methyl-1H-benzo[d]-imidazol-5-yl)but-1-enyl)phenol

Procedure

According to general procedure of McMurry reaction as example 1, step D described, 1-(1-methyl-1H-benzo[d]imidazol-5-yl)propan-1-one (730 mg, 2.2 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (500 mg, 1.0 eq) to give the separated (Z)-isomer and (E)-isomer of the product. (Z)-isomer: 1H NMR (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.62 (s, 1H), 7.11-7.15 (m, 3H), 7.01 (dd, J=8.4 Hz, 1.2 Hz, 1H), 6.83 (dd, J=6.8 Hz, 2.0 Hz, 2H), 6.79 (dd, J=6.8 Hz, 2.0 Hz, 2H), 6.49 (dd, J=6.8 Hz, 2.0 Hz, 2H), 4.05 (t, J=5.6 Hz, 2H), 3.79 (s, 3H), 3.69 (t, J=6.0 Hz, 2H), 2.53 (q, J=7.2 Hz, 2H), 0.91 (t, J=7.2 Hz, 3H).

Workup

  1. customAccording to general procedure of McMurry reaction as example 1, step D
  2. customto give the
  3. customseparated (Z)-isomer and (E)-isomer of the product

Sources & evidence

ORD record
ord-4d5f63b2f1e74426af3ef89de5618b6a
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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