Hydrochloric Acid → HCID 66742833, compound

HRID 1620829Notes

Reaction equation

HRID 1620829 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][N:20]([CH2:22][C:23]1C[C:26]([C:28]2[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=2[CH:30]=[O:31])=[CH:25][CH:24]=1)[CH3:21].[F:36][C:37]([Si](C)(C)C)([F:39])[F:38].Cl.C1C[O:48]CC1>>[CH3:21][N:20]([CH2:22][C:23]1[O:48][C:26]([C:28]2[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=2[CH:30]([OH:31])[C:37]([F:39])([F:38])[F:36])=[CH:25][CH:24]=1)[CH3:19]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 86621087HCID 86621087, compound

Product 1

HCID 66742833HCID 66742833, compoundYield 66%

Procedure

Tetrabutylammonium fluoride (0.013 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 2-(4-dimethylaminomethyl-cyclopenta-1,3-dienyl)-benzaldehyde (287 mg, 1.25) and trifluoromethyltrimethylsilane (TMSCF3) (222 μl, 1.5 mmol) in 5 ml THF at 0° C. The formed mixture was warmed up to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then treated with 5 ml of 1N HCl and stirred at room temperature overnight. The product was extracted with ethyl acetate (3×50 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 250 mg of 1-[2-(5-dimethylaminomethyl-furan-2-yl)-phenyl]-2,2,2-trifluoro-ethanol, yield 66%.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionThe product was extracted with ethyl acetate (3×50 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-26f32c0cfc3048b5920e6a6a4caaa9d1
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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