Tetrahydrofuran → 4-(2,2,2-Trifluoro-1-hydroxyethyl)pyridine-2-carbonitrile

HRID 1880763Notes

Reaction equation

HRID 1880763 reaction equation
O1CCCC1.[F:6][C:7]([F:26])([F:25])[CH:8]([C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]#[N:24])[CH:18]=1)[O:9][Si](CC)(CC)CC.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[F:26][C:7]([F:6])([F:25])[CH:8]([C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]#[N:24])[CH:18]=1)[OH:9]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 59570299HCID 59570299, compound

Product 1

HCID 595703134-(2,2,2-Trifluoro-1-hydroxyethyl)pyridine-2-carbonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 40 ml of tetrahydrofuran was added 12 g of 4-[2,2,2-trifluoro-1-(triethylsilyloxy)ethyl]pyridine-2-carbonitrile, and 15 ml of tetrabutylammonium fluoride (1M tetrahydrofuran solution) was added at 0° C. After the mixture was stirred at room temperature for 5 hours, water was added to the reaction solution, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 5.6 g of 4-(2,2,2-trifluoro-1-hydroxyethyl)pyridine-2-carbonitrile.

Workup

  1. additionwas added at 0° C
  2. extractionthe resultant solution was extracted with ethyl acetate three times
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bfd4c7ed51c245289040011f591f9028
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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