Dimethylformamide → 1-(triphenylmethyl)-1H-imidazole-2-carbaldehyde

HRID 1929640Notes

Reaction equation

HRID 1929640 reaction equation
[C:1]1([C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CN([CH:33]=[O:34])C.[NH4+].[Cl-]>C1COCC1.O.CCOCC>[C:7]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:33]=[O:34])([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 618231DechloroclotrimazoleHCID 178418339Butyllithium

Product 1

HCID 6182531-(triphenylmethyl)-1H-imidazole-2-carbaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (−78° C.) yellow solution of 1-(triphenylmethyl)imidazole (25.000 g; 80.542 mmol) in anhydrous THF (750 ml) was treated dropwise (in 55 min.) with a 1.6M solution of butyllithium in hexanes (55.35 ml; 88.560 mmol). After addition, the resulting pink homogeneous solution was further stirred at −78° C., under nitrogen, for 30 min. before a solution of anhydrous DMF (6.8 ml; 88.186 mmol) in anhydrous THF (40 ml) was added dropwise (in 40 min.). The resulting mixture was additionally stirred at −78° C., under nitrogen, for 1 h before aq. sat. NH4Cl (50 ml) was added dropwise. Ether (300 ml) and water (400 ml) were successively added, and this mixture was allowed to warm-up to rt. The yellow organic layer was additionally washed with water (300 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=30/1) to give the pure product 1-trityl-1H-imidazole-2-carbaldehyde as a pale yellow solid which was further dried under HV (20.660 g; 76%). LC-MS: tR=1.03 min.; [M+H]+: no ionisation.

Workup

  1. additionAfter addition
  2. additionwas added dropwise (in 40 min.)
  3. additionwas added dropwise
  4. washThe yellow organic layer was additionally washed with water (300 ml)
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe crude was purified by FC (DCM/MeOH=30/1)

Sources & evidence

ORD record
ord-c5afc143d20044bf843a26c16a5dada0
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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