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

HRID 1443319Notes

Reaction equation

HRID 1443319 reaction equation
C(O[K])(C)(C)C.[C:7](=[O:14])([O:11][CH2:12][CH3:13])OCC.C1(C)C=CC=CC=1.[C:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])[CH3:23]>O>[CH2:12]([O:11][C:7](=[O:14])[CH2:23][C:22](=[O:24])[C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)[CH3:13]

Participants

6

Reactant 4

HCID 1140TolueneHCID 69202-AcetylthiopheneHCID 7766Diethyl CarbonateHCID 178418922HCID 178418922, compound

Product 1

HCID 255159Ethyl 3-oxo-3-(thiophen-2-yl)propanoateYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
62.5 °C

Procedure

A 71.1 g (0.63 mol) portion of tert-butoxy potassium was added to 194.7 g (1.65 mol) of diethyl carbonate at 60 to 65° C. and stirred at 60 to 65° C. for 1 hour, and then 180 ml of toluene solution containing 50 g (0.40 mol) of 2-acetylthiophene was added dropwise thereto at 75 to 80° C. and stirred at 75 to 80° C. for 2 hours. The reaction solution was cooled down to room temperature, mixed with 725 g of water, extracted with 600 ml of ethyl acetate, washed with saturated brine, concentrated and then distilled under a reduced pressure to obtain 65.2 g of 3-oxo-3-(2-thienyl)propionic acid ethyl ester (yield 83%).

Workup

  1. additionwas added dropwise
  2. stirringat 75 to 80° C. and stirred at 75 to 80° C. for 2 hours
  3. temperatureThe reaction solution was cooled down to room temperature
  4. extractionextracted with 600 ml of ethyl acetate
  5. washwashed with saturated brine
  6. concentrationconcentrated
  7. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-80d1255e9aff46bc987bf0997e88c14b
Source dataset
uspto-grants-2010_02
Patent number
US07659409B2

Reaction notes

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