Water → 4-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyronitrile

HRID 2065408Notes

Reaction equation

HRID 2065408 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][CH2:7][C:8]([CH3:16])([CH3:15])[CH2:9]OS(C)(=O)=O)([CH3:4])([CH3:3])[CH3:2].[C-:19]#[N:20].[K+].O>CS(C)=O>[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][CH2:7][C:8]([CH3:16])([CH3:15])[CH2:9][C:19]#[N:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 574399153-(Tert-butyldimethylsilyloxy)-2,2-dimethylpropyl methanesulfonate

Product 1

HCID 109772134-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyronitrileYield 57.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propyl ester (5 g, 16.8 mmol) in anhydrous dimethyl sulfoxide (50 mL) was added KCN (2.85 g, 44 mmol). The reaction mixture was heated at 120° C. for 16 h. The mixture was cooled, and water was added. The mixture was extracted with ethyl acetate twice. The combined organic layers were washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:4) to give 4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyronitrile as a yellow oil (2.2 g, 57%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:hexanes=1:4)

Sources & evidence

ORD record
ord-824f5af5416940abbabde37cf9bc89f0
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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