Hydrochloric Acid → Ethyl 4-[4-(methylthio)phenyl]-2,4-dioxobutanoate

HRID 654772Notes

Reaction equation

HRID 654772 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].[H-].[Na+].[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>CN(C)C=O>[CH3:11][S:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 745011-(4-(Methylthio)phenyl)ethan-1-one

Product 1

HCID 10539688Ethyl 4-[4-(methylthio)phenyl]-2,4-dioxobutanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(methylthio)acetophenone 1 g) and sodium hydride (60%; 288 mg) in N,N-dimethylformamide (7 ml) was stirred at ambient temperature for 30 minutes. The mixture was cooled to 0° C., and diethyl oxalate (0.98 ml) was added dropwise to the mixture. The resulting mixture was stirred at ambient temperature for 3 hours, poured into ice-water and acidified with dilute hydrochloric acid. The precipitates were filtered, washed with water, and dried under reduced pressure to give a pale brown powder of ethyl 4-[4-(methylthio)phenyl]-2,4-dioxobutanoate (1.6 g).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe resulting mixture was stirred at ambient temperature for 3 hours
  3. filtrationThe precipitates were filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-dd18754b8b3e487a991bb8b3d1b4d692
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

Loading…