Potassium Cyanide → HCID 131728912, compound

HRID 551670Notes

Reaction equation

HRID 551670 reaction equation
[CH3:1][C@@:2]12[C:8](=[CH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][C@@H:6]1[CH2:5][CH:4]=[CH:3]2.[C-:17]#[N:18].[K+]>CS(C)=O.C(OCC)(=O)C>[C:17]([C@:8]1([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][C@H:6]2[C@:2]1([CH3:1])[CH:3]=[CH:4][CH2:5]2)#[N:18]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 131728911HCID 131728911, compound

Product 1

HCID 131728912HCID 131728912, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl(±)-[(1S,5R)-5-methyl-bicyclo[3.2.0]hept-3-en-6-ylidene]acetate (300 mg, 1.36 mmol) and potassium cyanide (89 mg, 1.36 mmol) were mixed at room temperature in anhydrous dimethyl sulfoxide (2 mL), and the mixture was stirred for 2 hours and then left overnight. The mixture was further stirred for 10 hours in an oil bath at 100° C. and then left overnight. The reaction solution was diluted with ethyl acetate, then washed with water and saturated saline, and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain the compound of interest as a colorless oil (128 mg). In this procedure, a by-product tert-butyl(±)-[(1S,5R,6R)-6-cyano-5-methyl-bicyclo[3.2.0]hept-3-en-6-yl]acetate was obtained as a colorless oil (45 mg).

Workup

  1. waitleft overnight
  2. stirringThe mixture was further stirred for 10 hours in an oil bath at 100° C.
  3. waitleft overnight
  4. washwashed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-abe92d1a43b9423a8466671f69417daa
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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