Sodium Acetate → HCID 71114867, compound

HRID 1624040Notes

Reaction equation

HRID 1624040 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[C:5]([CH3:12])[CH:4]=1)#[N:2].[CH3:13][C:14]1([CH3:21])[C:19](=[O:20])[CH:18]=[CH:17][CH2:16][CH2:15]1.C([O-])(=O)C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(=O)C>[CH3:13][C:14]1([CH3:21])[CH2:15][CH2:16][CH:17]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[CH3:12])[CH2:18][C:19]1=[O:20]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 117883026,6-Dimethyl-2-cyclohexen-1-oneHCID 16218401(4-Cyano-2-methyl-phenyl)boronic acid

Product 1

HCID 71114867HCID 71114867, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

4-Cyano-2-methylphenylboronic acid (0.81 g, 5 mmol), 6,6-dimethylcyclohex-2-enone (Canadian Journal of Chemistry, 1981, 59, 2096-2115) (0.55 g, 5 mmol), SbCl3 (0.11 g, 0.5 mmol), sodium acetate (0.82 g, 10 mmol), and palladium acetate (0.11 g, 0.5 mmol) are added to acetic acid (30 mL) under an atmosphere of argon. The reaction mixture is stirred at room temperature for three days. The mixture is filtered and the filtrate is poured into water (150 mL). The organic phase is separated and the aqueous phase is extracted with ethyl acetate (3×100 mL). The combined organic layers are washed with saturated sodium bicarbonate solution (3×100 mL), brine (3×50 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with pet ether: EtOAc=10:1 to give the title compound as a light yellow solid (0.6 g, 50%). GC/MS 241 (M+1).

Workup

  1. filtrationThe mixture is filtered
  2. additionthe filtrate is poured into water (150 mL)
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted with ethyl acetate (3×100 mL)
  5. washThe combined organic layers are washed with saturated sodium bicarbonate solution (3×100 mL), brine (3×50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. washeluting with pet ether

Sources & evidence

ORD record
ord-67fa1d576c1346b68ad1230482a1c228
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

Loading…