Tetrahydrofuran → 1-cyclohexyl-2,2,2-trifluoroethan-1-ol

HRID 1186364Notes

Reaction equation

HRID 1186364 reaction equation
[F-].[CH2:2]([N+](CCCC)(CCCC)CCCC)[CH2:3][CH2:4]C.[F:19][C:20]([Si](C)(C)C)([F:22])[F:21].[O:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:30]1([CH:31]([OH:27])[C:20]([F:22])([F:21])[F:19])[CH2:4][CH2:3][CH2:2][CH2:28][CH2:29]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 109430921-cyclohexyl-2,2,2-trifluoroethan-1-olYield 37%

Procedure

According to Reference Example 8-12, by use of cyclohexylcarbaldehyde (300 mg, 2.67 mmol) dissolved in tetrahydrofuran (6 mL), a 1 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (0.534 mL, 0.534 mmol) and (trifluoromethyl)trimethylsilane (0.474 mL, 3.20 mmol), the mixture was stirred and reacted at room temperature for 1.5 hours. Then, purification by preparative thin-layer chromatography (hexane/ethyl acetate=10/1) was performed to give 1-cyclohexyl-2,2,2-trifluoroethanol (Compound DP) (181 mg, yield: 37%).

Workup

  1. customreacted at room temperature for 1.5 hours
  2. customThen, purification by preparative thin-layer chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-d207a68bb9d147f99e74f4ffa9b4d8a2
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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