Potassium Hydroxide → (E)-1-(1-Methyl-1H-indol-3-yl)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-2-propen-1-one

HRID 1382788Notes

Reaction equation

HRID 1382788 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH:26]=O.[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:38](=[O:40])[CH3:39])=[CH:30]1.[OH-].[K+]>C(O)C.O>[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:38](=[O:40])/[CH:39]=[CH:26]/[C:3]2[N:4]=[CH:5][N:6]([C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:2]=2[CH3:1])=[CH:30]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 5941561-(1-Methyl-1H-indol-3-yl)ethanoneHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 21273210(E)-1-(1-Methyl-1H-indol-3-yl)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-2-propen-1-oneYield 133.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-methyl-1-(triphenylmethyl)-1H-imidazole-4-carboxaldehyde (2.5 g), 1-(1-methyl-1H-indol-3-yl)-1-ethanone (1.0 g) and potassium hydroxide (3.1 g) in absolute ethanol (50 ml) and water (25 ml) was stirred at room temperature for 72 h, then at 50° for 18 h. The mixture was partitioned between 2N sodium carbonate (200 ml) and ethyl acetate (2×200 ml) and the combined organic layers were washed with brine (150 ml), dried and evaporated in vacuo to leave a foam (3.9 g) which was purified by FCC eluting with ethyl acetate:hexane (1:1) to give the title compound (1.76 g) as a solid, m.p. 216°-219°.

Workup

  1. waitat 50° for 18 h
  2. customThe mixture was partitioned between 2N sodium carbonate (200 ml) and ethyl acetate (2×200 ml)
  3. washthe combined organic layers were washed with brine (150 ml)
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8e88b9b1c98740d38a28c6d759d6db48
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

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