Methyltriphenylphosphonium iodide → HCID 20432318, compound

HRID 2412502Notes

Reaction equation

HRID 2412502 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[PH5].[F:29][C:30]1[N:31]([C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:32]=[C:33]([CH:35]=O)[N:34]=1>CS(C)=O>[F:29][C:30]1[N:31]([C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:32]=[C:33]([CH:35]=[CH2:2])[N:34]=1

Participants

6

Reactant 4

HCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehydeHCID 178527699HCID 178527699, compound

Product 1

HCID 20432318HCID 20432318, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl triphenylphosphonium iodide was treated with potassium t-butoxide in DMSO. After generation of the phosphorane, 2-fluoro-4-formyl-1-triphenylmethylimidazole was added, and the mixture heated 2 hours at 60°. Extractive work-up and chromatography gave 2-fluoro-1-triphenylmethyl-4-vinylimidazole, having the following n.m.r. in CDCl3 : 5.1 (d, 1H); 5.77 (d, 1H); 6.26-6.63 (m, 1H); 6.48 (s, 1H); 7.1-7.5 (m, 15H).

Workup

  1. temperaturethe mixture heated 2 hours at 60°

Sources & evidence

ORD record
ord-3526859f8fbd4323b79d6852fceb5d98
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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