Toluene → HCID 20432326, compound

HRID 2412483Notes

Reaction equation

HRID 2412483 reaction equation
[F:1][C:2]1[N:3]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=[C:5](C=O)[N:6]=1.C(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:30])C.[C:50]1(C)C=C[CH:53]=[CH:52][CH:51]=1>>[F:1][C:2]1[N:3]([C:9]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:4]=[C:5](/[CH:50]=[CH:51]/[C:52](=[O:30])[CH3:53])[N:6]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehydeHCID 178476776HCID 178476776, compound

Product 1

HCID 20432326HCID 20432326, compound

Procedure

2-Fluoro-4-formyl-1-triphenylmethylimidazole and acetyl triphenyl phosphorane were reacted in toluene at 100° over 18 hours to give E-2-fluoro-4-(3-oxobut-1-enyl)-1-triphenylmethylimidazole. This was hydrogenated in a mixture of EtOAC and EtOH, using 5% w/w palladium on carbon as catalyst, to give 2-fluoro-4-(3-oxobutyl)-1-triphenylmethylimidazole. This was treated in EtOH with O-methylhydroxylamine hydrochloride and pyridine. Evaporation of solvent and trituration with water gave 2-fluoro-4-(3-methoxyiminobutyl)-1-triphenylmethylimidazole as a mixture of isomers, the major Z-isomer having the following n.m.r. spectrum in CDCl3 : 1.84 (s, 3H); 2.4-2.7 (m, 4H); 3.86 (s, 3H); 6.37 (s, 1H); 7.1-7.4 (m, 15H).

Sources & evidence

ORD record
ord-6a6b516d411045238e2d293e6e56a667
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

Loading…