Potassium Carbonate → 2-Methyl-2-(4-(4-methyloxazol-5-yl)phenyl)propanenitrile

HRID 1672561Notes

Reaction equation

HRID 1672561 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])=[CH:5][CH:4]=1)=[O:2].[N+:14]([CH:16](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:17])#[C-:15].C([O-])([O-])=O.[K+].[K+]>CO>[CH3:12][C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]2[O:2][CH:15]=[N:14][C:16]=2[CH3:17])=[CH:4][CH:5]=1)([CH3:13])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzeneHCID 729428052-(4-formylphenyl)-2-methylpropanenitrile

Product 1

HCID 666966892-Methyl-2-(4-(4-methyloxazol-5-yl)phenyl)propanenitrileYield 80.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 35B (2.24 g, 12.9 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (2.71 g, 12.9 mmol), and K2CO3 (2.15 g, 15.5 mmol) in MeOH (60 mL) was heated at reflux for 2 hr. The reaction was cooled to ambient temperature, and the volatiles removed at reduced pressure. The residue was partitioned between H2O and Et2O. The separated aqueous phase was extracted with Et2O, and the combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280™; 15% to 40% EtOAc/hexanes eluant; SF40-150 g column) yielded 2.35 g (80%) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 8.35 (s, 1H), 7.71-7.61 (m, 4H), 2.37 (s, 3H), 1.71 (s, 6H). MS (DCI+) m/z 227 (M+H).

Workup

  1. temperatureat reflux for 2 hr
  2. customthe volatiles removed at reduced pressure
  3. customThe residue was partitioned between H2O and Et2O
  4. extractionThe separated aqueous phase was extracted with Et2O
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64a5f57145e14d9283cf116e0cca1e32
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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