(Trifluoromethyl)trimethylsilane → 2,2,2-Trifluoro-1-(4-methyloxan-4-yl)ethan-1-ol

HRID 1186382Notes

Reaction equation

HRID 1186382 reaction equation
[CH3:1][C:2]1([CH:8]=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:28][C:29]([Si](C)(C)C)([F:31])[F:30]>O1CCCC1>[F:28][C:29]([F:31])([F:30])[CH:8]([C:2]1([CH3:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1)[OH:9]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 205923884-Methyloxane-4-carbaldehyde

Product 1

HCID 674021352,2,2-Trifluoro-1-(4-methyloxan-4-yl)ethan-1-olYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 4-methyltetrahydro-2H-pyran-4-carbaldehyde (165 mg, 1.29 mmol) dissolved in tetrahydrofuran (5 mL), a 1 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (0.258 mL, 0.258 mmol) and (trifluoromethyl)trimethylsilane (0.229 mL, 1.55 mmol), the mixture was stirred and reacted at room temperature for 1.7 hours. Then, purification by extraction gave 2,2,2-trifluoro-1-(4-methyltetrahydro-2H-pyran-4-yl)ethanol (Compound EC) (119 mg, yield: 47%).

Workup

  1. customreacted at room temperature for 1.7 hours
  2. customThen, purification
  3. extractionby extraction

Sources & evidence

ORD record
ord-1c629aebad5f45d1bae09b6c75e861ac
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…