Cyclopropanecarboxaldehyde → 1-cyclopropyl-2,2,2-trifluoroethan-1-ol

HRID 1186380Notes

Reaction equation

HRID 1186380 reaction equation
[CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:24][C:25]([Si](C)(C)C)([F:27])[F:26]>O1CCCC1>[CH:1]1([CH:4]([OH:5])[C:25]([F:27])([F:26])[F:24])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 157096431-cyclopropyl-2,2,2-trifluoroethan-1-olYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of cyclopropanecarbaldehyde (300 mg, 4.28 mmol) dissolved in tetrahydrofuran (6 mL), a 1 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (0.856 mL, 0.856 mmol) and (trifluoromethyl)trimethylsilane (0.759 mL, 5.14 mmol), the mixture was stirred and reacted at room temperature for 1.7 hours. Then, purification by extraction gave 1-cyclopropyl-2,2,2-trifluoroethanol (Compound EB) (161 mg, yield: 27%).

Workup

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

Sources & evidence

ORD record
ord-487d1e5fca3e4a86a00abafb837f0536
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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