Trifluoroacetic acid → HCID 178519948, compound

HRID 868930Notes

Reaction equation

HRID 868930 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:31]=[O:32])[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[C:9]([CH:31]=[O:32])[NH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10740521HCID 10740521, compound

Product 1

HCID 178519948HCID 178519948, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenyl-1-trityl-1H-imidazole-2-carbaldehyde (414 mg, 1 mmol) in DCM (10 mL) was added 2,2,2-trifluoroacetic acid (1 mL). After stirring at room temperature for 30 minutes, the solvent was removed in vacuo. The resulting residue was diluted with DCM (50 mL) and saturated sodium bicarbonate (50 mL). The aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were dried over sodium sulfate, filtered, concentrated and then purified by column chromatography to give 4-phenyl-1H-imidazole-2-carbaldehyde as a white solid (160 mg). MS (ESI): m/z 173 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe resulting residue was diluted with DCM (50 mL) and saturated sodium bicarbonate (50 mL)
  3. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-ef9711135a1c4eafaf75b37b4030c1dd
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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