(Trifluoromethyl)trimethylsilane → HCID 62390560, compound

HRID 1186379Notes

Reaction equation

HRID 1186379 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[O:8])[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:27][C:28]([Si](C)(C)C)([F:30])[F:29]>O1CCCC1>[F:27][C:28]([F:30])([F:29])[CH:7]([CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[OH:8]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 62390560HCID 62390560, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of tetrahydro-2H-pyran-4-carbaldehyde (300 mg, 2.63 mmol) dissolved in tetrahydrofuran (6 mL), a 1 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (0.526 mL, 0.526 mmol) and (trifluoromethyl)trimethylsilane (0.466 mL, 3.16 mmol), the mixture was stirred and reacted at room temperature for 1.7 hours. Then, purification by preparative thin-layer chromatography (hexane/ethyl acetate=4/1) was performed to give 2,2,2-trifluoro-1-(tetrahydro-2H-pyran-4-yl)ethanol (Compound EA) (228 mg, yield: 47%).

Workup

  1. customreacted at room temperature for 1.7 hours
  2. customThen, purification by preparative thin-layer chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-da18f34e0af0443a9291c589f42e2439
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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