Bis(2-chloroethyl) ether → 4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1868735Notes

Reaction equation

HRID 1868735 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:19])([F:18])[C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1.Cl[CH2:21][CH2:22][O:23][CH2:24][CH2:25]Cl>CN(C=O)C>[F:7][C:8]([F:18])([F:19])[C:9]1[CH:10]=[C:11]([C:15]2([C:16]#[N:17])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 75360m-TrifluoromethylphenylacetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 431190344-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-carbonitrileYield 162.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (4.00 g, 35.6 mmol, 2.20 eq) was added to a stirred solution of 2-(3-(trifluoromethyl)phenyl)acetonitrile (2.53 mL, 16.2 mmol, 1.0 eq) in DMF (30 mL) at 0° C. under a nitrogen atmosphere. The mixture was stirred for 10 minutes at 0° C. before 1-chloro-2-(2-chloroethoxy)ethane (2.09 mL, 17.8 mmol, 1.1 eq) was added dropwise via syringe. The reaction mixture was allowed to warm to room temperature and stirred for 6 hours. The reaction mixture was then cooled to 0° C. and quenched with 10% HCl. The aqueous mixture was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo to give the product as an orange oil (6.73 g).

Workup

  1. additionwas added dropwise via syringe
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customquenched with 10% HCl
  4. extractionThe aqueous mixture was extracted with EtOAc (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dd31b911c7a4906afba1af53011c2d8
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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