Dimethylformamide → 2-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

HRID 1463164Notes

Reaction equation

HRID 1463164 reaction equation
[F:1][C:2]1[N:3]([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:4]=[CH:5][N:6]=1.C([Li])(C)(C)C.CN([CH:34]=[O:35])C>C1COCC1.CCCCC.CCOCC>[CH:34]([C:5]1[N:6]=[C:2]([F:1])[N:3]([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:4]=1)=[O:35]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 20432454HCID 20432454, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-fluoro-1-triphenylmethylimidazole (3.28 g.) in dry THF (33 ml.) was treated, under argon, at -75° with two equivalents of t-butyl lithium (10 ml. of a 1.93M solution in pentane). After stirring 3 hours at -75°, DMF (1.5 ml.) was added. The reaction mixture was kept a further hour at -75° then allowed to warm up slowly to room temperature. The reaction was worked up by diluting with ether, washing with 2N HCl followed by brine. The ether layer was concentrated under a steam of argon to give 4-formyl-2-fluoro-1-triphenylmethylimidazole, (2.2 g.) m.p. 177°-179°.

Workup

  1. waitThe reaction mixture was kept a further hour at -75°
  2. washwashing with 2N HCl
  3. concentrationThe ether layer was concentrated under a steam of argon

Sources & evidence

ORD record
ord-8cdc0af79e5c409da9b8245fc4fa6fcf
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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