Thionyl Chloride → 2-(dihydro-2H-pyran-4(3H)-ylidene)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile

HRID 512173Notes

Reaction equation

HRID 512173 reaction equation
O[C:2]1([CH:8]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[C:9]#[N:10])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O>CN(C=O)C>[O:5]1[CH2:4][CH2:3][C:2](=[C:8]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)[C:9]#[N:10])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86716199(4-Hydroxy-tetrahydro-pyran-4-yl)-(6-trifluoromethyl-pyridin-3-yl)-acetonitrile

Product 1

HCID 867162002-(dihydro-2H-pyran-4(3H)-ylidene)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

(4-Hydroxy-tetrahydro-pyran-4-yl)-(6-trifluoromethyl-pyridin-3-yl)-acetonitrile (1.15 g, 4.02 mmol) was dissolved in thionyl chloride (50 mL, 600 mmol). One drop of DMF was added and the mixture was heated at reflux for 1 hour and then cooled to room temperature and concentrated in vacuo. The resulting crude product was purified by flash chromatography to yield 2-(dihydro-2H-pyran-4(3H)-ylidene)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile (1.04 g, 3.9 mmol, 95%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5ac7defc4f4f426ca6b46cbc3c7b9b12
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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