Dimethylformamide → 4-(2-Cyanovinyl)-2-fluoro-1-triphenylmethyl imidazole

HRID 2412481Notes

Reaction equation

HRID 2412481 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].CN(C=O)C.[F:19][C:20]1[N:21]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=[C:23]([CH:25]=O)[N:24]=1>C(COC)OC>[C:1]([CH:3]=[CH:25][C:23]1[N:24]=[C:20]([F:19])[N:21]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1)#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 537196044-(2-Cyanovinyl)-2-fluoro-1-triphenylmethyl imidazole

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Examples 15 and 16: Diethyl cyanomethylphosphonate was converted to its anion with sodium hydride in dimethoxyethane solution. An equal volume of DMF was added, followed by 2-fluoro-4-formyl-1-triphenylmethylimidazole. Reaction at room temperature gave 4-(2-cyanovinyl)-2-fluoro-1-triphenylmethyl imidazole. A suspension of this in MeOH was reduced by magnesium turnings to give 4-(2-cyanoethyl)-2-fluoro-1-triphenylmethylimidazole, having the following n.m.r. spectrum in CDCl3 : 2.71 (t, 4H); 6.42 (s, 1H); 7.1-7.4 (m, 15H).

Workup

  1. customReaction at room temperature

Sources & evidence

ORD record
ord-120b4f44339c4d94b36c868e746a45ba
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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