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

HRID 1186364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186364
[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

Komponenten

4

Edukt 3

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

Produkt 1

HCID 109430921-Cyclohexyl-2,2,2-trifluoroethan-1-olAusbeute 37 %

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d207a68bb9d147f99e74f4ffa9b4d8a2
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673908B2

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