Phenylacetonitrile → 2-Phenyl-4-trimethylsilanyloxy-butyronitrile

HRID 2242790Notes

Reaction equation

HRID 2242790 reaction equation
CC(C)([O-])C.[K+].[C:7]1([CH2:13][C:14]#[N:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:17][CH2:18][O:19][Si:20]([CH3:23])([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[C:7]1([CH:13]([CH2:17][CH2:18][O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:14]#[N:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 587231(2-Bromoethoxy)trimethylsilaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 687466832-Phenyl-4-trimethylsilanyloxy-butyronitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of potassium tert-butoxide (12.3 g) in toluene (200 mL) was treated dropwise with a mixture of phenylacetonitrile (12.9 g) and (2-bromoethoxy)trimethyl-silane (23.8 g) at room temperature. Upon completion of the addition, the reaction mixture was refluxed for 5 h, then cooled to room temperature and quenched by pouring onto a mixture of ice and water. The formed organic phase was separated and the aqueous phase was extracted with benzene. The combined organic phases were washed with water, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator to give 2-phenyl-4-trimethylsilanyloxy-butyronitrile. The obtained butyronitrile derivative was redissolved in a mixture of ethanol (40 mL) and 70% aqueous sulfuric acid (40 mL), stirred at 50° C. for 3 h and, after cooling to room temperature, diluted with water (150 mL). The resulted organic phase was separated and the aqueous phase was extracted with benzene. The combined organic phases were washed with water, then with saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator and distilled in vacuum to give 11.0 g (62%) of the title compound.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was refluxed for 5 h
  3. customquenched
  4. additionby pouring onto a mixture of ice and water
  5. customThe formed organic phase was separated
  6. extractionthe aqueous phase was extracted with benzene
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-d9103fbac84b443a8c956d16ea893054
Source dataset
uspto-grants-2010_03
Patent number
US07674741B2

Reaction notes

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