Cyclohexyl methyl ketone → HCID 58495622, compound

HRID 1190997Notes

Reaction equation

HRID 1190997 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH:10]1([C:16](=[O:18])[CH3:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH:10]1([C:16](=[O:18])[CH2:17][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 3

HCID 13207Cyclohexyl methyl ketone2×HCID 764674-IodobenzonitrileHCID 23676156Sodium t-butoxide2×

Product 1

HCID 58495622HCID 58495622, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-Catalyst2×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Add 4-iodobenzonitrile (1.0 g, 4.37 mmol) and 1-cyclohexyl-ethanone (717 mg, 5.68 mmol) to a suspension of tris(dibenzylideneacetone)dipalladium(0) (60 mg, 0.065 mmol), BINAP (98 mg, 0.157 mmol) and sodium tert-butoxide (546 mg, 5.68 mmol) in anhydrous THF (26 mL). Heat the mixture at 70° C. under nitrogen atmosphere. After 6 h, add tris(dibenzylideneacetone)dipalladium(0) (60 mg, 0.065 mmol), BINAP (98 mg, 0.157 mmol), sodium tert-butoxide (294 mg, 3.06 mmol) and 1-cyclohexyl-ethanone (386 mg, 3.06 mmol) and allow to stir the mixture at 70° C. under nitrogen overnight. Add water and extract twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (92:8) to obtain the desired intermediate as a yellow oil (902 mg, 91%).

Workup

  1. extractionAdd water and extract twice with EtOAc
  2. dry with materialDry the combined organic extracts over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (92:8)

Sources & evidence

ORD record
ord-2e7133c80fdc475d86d5201abbb4cffb
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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