Water → HCID 71291688, compound

HRID 1502559Notes

Reaction equation

HRID 1502559 reaction equation
C([O-])C.[Na+].[CH3:5][C:6]1[S:10][C:9]([C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:7]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].O>C(O)C>[CH3:5][C:6]1[S:10][C:9]([C:11]([CH:12]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:18])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 2723922Sodium ethoxideHCID 33785864HCID 33785864, compound

Product 1

HCID 71291688HCID 71291688, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.54 g of sodium ethanolate (22.6 mmol), 4.00 g ethyl 3-(5-methylthiophen-2-yl)-3-oxopropanoate (2) and 6.67 g of ethyl bromoacetate are suspended under argon in absolute ethanol at 0° C. The mixture is stirred overnight. Water is added, ethanol is evaporated and the aqueous solution is extracted with diethyl ether. The organic phase is washed with water containing few drops of concentrated HCl, dried and evaporated to provide diethyl 2-(5-methylthiophene-2-carbonyl)succinate (3) which is used without further purification. A mixture of compound 3 and 11.64 g of ammonium acetate in glacial acetic acid is stirred at 120° C. under argon for 4 hours. After cooling to room temperature, the mixture is poured into water. The precipitate formed is isolated by filtration, washed with water and diethyl ether to provide compound 4. 1H NMR (300 MHz, CDCl3) δ 9.57 1H s, 7.61 1H d, 6.81 1H m, 4.24 2H q, 3.53 2H s, 2.54 3H large s, 1.31 3H t.

Workup

  1. customethanol is evaporated
  2. extractionthe aqueous solution is extracted with diethyl ether
  3. washThe organic phase is washed with water containing few drops of concentrated HCl
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-a1c60d5a3a5844969ef05dc853228cd8
Source dataset
uspto-grants-2015_12
Patent number
US09209412B2

Reaction notes

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