3-Furancarboxaldehyde, tetrahydro- → 1226507-56-7

HRID 1186389Notes

Reaction equation

HRID 1186389 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH:6]=[O:7])[CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:26][C:27]([Si](C)(C)C)([F:29])[F:28]>O1CCCC1>[F:26][C:27]([F:29])([F:28])[CH:6]([CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)[OH:7]

Participants

5

Reactant 3

HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 616452131226507-56-7Yield 31.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of a 50 wt % aqueous tetrahydrofuran-3-carbaldehyde solution (1.00 g, 5.00 mmol) dissolved in tetrahydrofuran (15 mL), a 1 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (1.00 mL, 1.00 mmol) and (trifluoromethyl)trimethylsilane (0.887 mL, 6.00 mmol), the mixture was stirred and reacted at room temperature for 1.8 hours. Then, purification by extraction gave 2,2,2-trifluoro-1-(tetrahydrofuran-3-yl)ethanol (Compound EJ) (266 mg, yield: 31%).

Workup

  1. customreacted at room temperature for 1.8 hours
  2. customThen, purification
  3. extractionby extraction

Sources & evidence

ORD record
ord-a92888a5540e4cb0bc4d283205e61c92
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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