2-Acetylthiophene → Ethyl 3-oxo-3-(thiophen-2-yl)propanoate

HRID 1443318Notes

Reaction equation

HRID 1443318 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[C:11]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)(=[O:13])[CH3:12]>O1CCCC1>[CH2:8]([O:7][C:3](=[O:10])[CH2:12][C:11](=[O:13])[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[CH3:9]

Participants

5

Reactant 3

HCID 69202-AcetylthiopheneHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 255159Ethyl 3-oxo-3-(thiophen-2-yl)propanoateYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 0.254 g portion of 60% sodium hydride and 1.95 g of diethyl carbonate were charged using 1.0 ml of tetrahydrofuran at 24° C. and then the temperature was increased to carry out reflux. At said temperature (79° C.) a solution prepared by dissolving 0.5 g of 2-acetylthiophene in 1 ml of tetrahydrofuran was added dropwise thereto spending 15 minutes. Thereafter, the mixture was stirred at said temperature for 1 hour, and when the reaction was completed, the reaction solution was analyzed by a liquid chromatography under the same conditions of the aforementioned Production Example 1 to find that the reaction yield was 89%.

Workup

  1. customat 24° C.
  2. temperaturethe temperature was increased
  3. temperatureto carry out reflux
  4. customtemperature (79° C.)
  5. customprepared
  6. additionwas added dropwise
  7. customfor 1 hour
  8. customto find that the reaction yield was 89%

Sources & evidence

ORD record
ord-be06319041b143fa853855866c96274a
Source dataset
uspto-grants-2010_02
Patent number
US07659409B2

Reaction notes

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