Potassium Carbonate → 2-[4-(5-Oxazolyl)phenyl]-2-methyl-1,3-dioxolane

HRID 497208

Reaction equation

HRID 497208 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:14])[O:13][CH2:12][CH2:11][O:10]2)=[CH:5][CH:4]=1)=[O:2].S([CH2:25][N+:26]#[C-:27])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[O:2]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]([C:9]3([CH3:14])[O:10][CH2:11][CH2:12][O:13]3)=[CH:7][CH:8]=2)=[CH:27][N:26]=[CH:25]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 119615844-(2-Methyl-1,3-dioxolan-2-yl)benzaldehyde

Product 1

HCID 223167142-[4-(5-Oxazolyl)phenyl]-2-methyl-1,3-dioxolaneYield 37.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-(4-formylphenyl)-2-methyl-1,3-dioxolane (1.58 g, 8.23 mmol) in methanol (10 ml) was added tosylmethyl isocyanide (2.0 g, 10.3 mmol), potassium carbonate (1.42 g, 10.3 mmol), and the mixture was heated at reflux temperature for 2 hours. The reaction mixture was diluted with water and the whole was extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:4) to give the title compound (711 mg, 37% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 2 hours
  3. extractionthe whole was extracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-e359f5e4807b41ab839d44e9ee5ccb61
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Linked notes

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