Potassium Cyanide → HCID 23031266, compound

HRID 1766675Notes

Reaction equation

HRID 1766675 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20](I)=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[CH:11][C:10]=1[CH:27]([CH3:29])[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:30]#[N:31].[K+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CN1CCCC1=O>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[C:15]3[CH2:16][CH2:17][CH2:18][C:19]=3[C:20]([C:30]#[N:31])=[CH:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH:27]([CH3:29])[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 23031219HCID 23031219, compound

Product 1

HCID 23031266HCID 23031266, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-(4-benzyloxy-3-isopropylphenoxy)-7-iodo-5-methylindane (214 mg), potassium cyanide (60 mg), bis(dibenzylidenacetone)palladium (4 mg), 1,1′-bis(diphenylphosphino) ferrocene (8 mg), and 1-methyl-2-pyrrolidone (2 mL) were stirred under an argon atmosphere at 80° C. overnight. Adding water, the reaction mixture was extracted with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate) to give the title compound (49 mg).

Workup

  1. extractionAdding water, the reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a11f7e40e7f0494481783cb4dab99236
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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