Dimethyl Sulfoxide → 3-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]propanenitrile

HRID 337588Notes

Reaction equation

HRID 337588 reaction equation
CS(C)=O.CS(O[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:15]([Cl:27])=[C:14]([Cl:28])[CH:13]=1)(=O)=O.[C-:29]#[N:30].[K+]>CCOCC>[Cl:28][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][C:29]#[N:30])[CH:17]=[C:16]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:15]=1[Cl:27]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 866516682-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate

Product 1

HCID 668961283-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]propanenitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a DMSO (0.4 M) solution of 2-[3,4-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate (1 eq.) from the previous step was added potassium cyanide (1.3 eq.). The resulting solution was stirred at 80° C. for 4 h. The reaction was then diluted with ether and quenched with water. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to give the title compound as a pink oil.

Workup

  1. customquenched with water
  2. customThe aqueous layer was separated
  3. extractionback-extracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2f3969eacae24e35b5c68cc8f3c80755
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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