(Trifluoromethyl)trimethylsilane → HCID 58319192, compound

HRID 2363148Notes

Reaction equation

HRID 2363148 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12].C[Si](C)(C)[C:15]([F:18])([F:17])[F:16].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2([C:15]([F:18])([F:17])[F:16])[OH:12]

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 58319192HCID 58319192, compoundYield 59,522.801%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cold suspension of 4-methoxy-indan-1-one (200 mg, 1.23 mmol) and trimethyl(trifluoromethyl)silane (218 mg, 1.48 mmol) in THF (4 mL) was added 1M-TBAF (615 mL, 0.615 mmol) at 0° C. The mixture was stirred overnight at room temperature, and then diluted with EtOAc. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated tinder reduced pressure. The crude residue was purified by column chromatography to give 4-methoxy-1-trifluoromethyl-indan-1-ol (170 g, 60%).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated tinder reduced pressure
  5. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-532ad736498048a89db419e04222a53b
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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