Acetic Acid → HCID 10261796, compound

HRID 2292648Notes

Reaction equation

HRID 2292648 reaction equation
[H-].[Na+].[C:3]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)(=[O:5])[CH3:4].C(O)(=O)C.[C:15](=O)([O:18]C)[O:16][CH3:17]>>[S:8]1[CH:9]=[CH:10][C:6]([C:3](=[O:5])[CH2:4][C:15]([O:16][CH3:17])=[O:18])=[CH:7]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 151161-(Thiophen-3-yl)ethanoneHCID 24758Sodium hydride

Product 1

HCID 10261796HCID 10261796, compoundYield 46%

Procedure

24 g (0.6 mmol) of sodium hydride (60%) are added in portions at 0° C., over a period of 10 minutes, to 25.2 g (0.2 mmol) of 3-acetylthiophene in 600 ml of dimethyl carbonate, and then the whole is heated at reflux for 30 minutes, allowed to cool and poured into 1 liter of a water/ice mixture containing 53 ml of acetic acid. Extraction is carried out 3 times with 250 ml of ether each time. The combined organic phases are dried over magnesium sulphate. After evaporation, the residue is chromatographed on silica (eluant:dichloromethane) to yield 17 g of the desired compound (yield: 46%).

Workup

  1. temperaturethe whole is heated
  2. temperatureat reflux for 30 minutes
  3. temperatureto cool
  4. extractionExtraction
  5. dry with materialThe combined organic phases are dried over magnesium sulphate
  6. customAfter evaporation
  7. customthe residue is chromatographed on silica (eluant:dichloromethane)

Sources & evidence

ORD record
ord-252eeb6f40c94f498f1c6755e2eeef14
Source dataset
uspto-grants-1997_11
Patent number
US05684020

Reaction notes

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