Potassium Cyanide → HCID 68958470, compound

HRID 2378058Notes

Reaction equation

HRID 2378058 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3([CH2:25]OS(C)(=O)=O)[CH2:24][CH2:23]3)[O:13][N:12]=2)=[CH:7][CH:6]=1.[C-:31]#[N:32].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:14]([C:22]3([CH2:25][C:31]#[N:32])[CH2:23][CH2:24]3)[O:13][N:12]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 86613311HCID 86613311, compound

Product 1

HCID 68958470HCID 68958470, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture consisting of methanesulfonic acid 1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl ester (synthetic intermediate prepared in Example 11, Step iv, 0.45 g) in N,N-dimethylformamide (4 mL) is added potassium cyanide (0.17 g.) The mixture is stirred at 80° C. for five hours and is subsequently diluted with ethyl acetate (30 mL.) The mixture is sequentially washed with water (15 mL) and brine solution (15 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the synthetic intermediate {1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropyl}-acetonitrile (0.38 g.)

Workup

  1. washis sequentially washed with water (15 mL) and brine solution (15 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6fa93f1836e04ef4a8ba4d260298c37a
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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