(Trifluoromethyl)trimethylsilane → HCID 54108533, compound

HRID 2298541Notes

Reaction equation

HRID 2298541 reaction equation
C1(C([NH:20][C:21]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:22]=2[CH:23]=[O:24])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:30][C:31]([Si](C)(C)C)([F:33])[F:32].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:22]=1[CH:23]([OH:24])[C:31]([F:33])([F:32])[F:30]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 18386569HCID 18386569, compound

Product 1

HCID 54108533HCID 54108533, compoundYield 175.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-triphenylmethylamino-6-fluorobenzaldehyde (100 mg, 0.24 mmol) in THF (2 mL) at 0° C. was added trifluoromethyltrimethylsilane (0.06 mL, 0.36 mmol) followed by a solution of tetrabutylammonium fluoride in THF (1M, 0.36 mL, 0.36 mmol) and the resulting reaction mixture was allowed to stir with warming to room temperature (ice bath removed after the addition of reagents) for 0.5 h. The reaction mixture was poured onto water and extracted with EtOAc (3×50 mL) and the combined EtOAc extracts were dried over anhydrous NaSO4 and concentrated in vacuo. Chromatography (SiO2, 10% EtOAc-hexanes) provided 88 mg of the title compound (108 mg theoretical, 82% yield).

Workup

  1. customthe resulting reaction mixture
  2. customremoved
  3. additionafter the addition of reagents) for 0.5 h
  4. additionThe reaction mixture was poured onto water
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialthe combined EtOAc extracts were dried over anhydrous NaSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f69ac0d04fd4697be39b8580cfa16c0
Source dataset
uspto-grants-2002_12
Patent number
US06492515B2

Reaction notes

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