Water → HCID 68940694, compound

HRID 883183Notes

Reaction equation

HRID 883183 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH3:8][C:9]([CH3:14])([CH3:13])[C:10](=[O:12])[CH3:11].C[O-].[Na+].O>CO>[CH3:8][C:9]([CH3:14])([CH3:13])[C:10](=[O:12])[CH:11]=[CH:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6416PinacoloneHCID 681353-ThiophenecarboxaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 68940694HCID 68940694, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Thiophene carbaldehyde (500 μL, 5.71 mmol) and 3,3-dimethylbutan-2-one (710 μL, 5.71 mmol) were dissolved in methanol (5.0 mL). To this was added sodium methoxide (340 mg, 6.29 mmol), and then the mixture was stirred under reflux overnight. After addition of water, the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated off in vacuo. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate 95/5) to give the title compound (904 mg, 4.65 mmol, yield 81%).

Workup

  1. temperatureunder reflux overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated off in vacuo
  6. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate 95/5)

Sources & evidence

ORD record
ord-d8b328883fdc46a79720b1a6ffc405c4
Source dataset
uspto-grants-2012_08
Patent number
US08236841B2

Reaction notes

Loading…