Hydrochloric Acid → 1-[4-(6-Methoxy-pyridine-2-yl)-phenyl]-2,2,2-trifluoro-ethanol

HRID 2233470Notes

Reaction equation

HRID 2233470 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]1[N:26]=[C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=2)[CH:24]=[CH:23][CH:22]=1.[F:35][C:36]([Si](C)(C)C)([F:38])[F:37].Cl>C1COCC1>[CH3:19][O:20][C:21]1[N:26]=[C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH:31]([OH:32])[C:36]([F:38])([F:37])[F:35])=[CH:29][CH:28]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 36758234-(6-Methoxy-2-pyridinyl)benzaldehyde

Product 1

HCID 667436631-[4-(6-Methoxy-pyridine-2-yl)-phenyl]-2,2,2-trifluoro-ethanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (TBAF) (0.1 ml of 1M in THF) was added to a solution of 4-(6-methoxy-pyridine-2-yl)-benzaldehyde (213 mg, 1 mmol) and trifluoromethyl trimethylsilane (0.2 ml, 1.2 mmol) in 10 ml THF at 0° C. The mixture was warmed up to room temperature and stirred for 4 hours. The reaction mixture was then treated with 12 ml of 1M HCl and stirred overnight. The product was extracted with ethyl acetate (3×20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 0.25 g of 1-[4-(6-methoxy-pyridine-2-yl)-phenyl]-2,2,2-trifluoro-ethanol which was directly used in next step without purification. yield: 90%.

Workup

  1. stirringstirred overnight
  2. extractionThe product was extracted with ethyl acetate (3×20 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-939b0c4c3e1b44cfb6754caf2336f8fc
Source dataset
uspto-grants-2010_05
Patent number
US07709493B2

Reaction notes

Loading…