Ethoxalyl chloride → HCID 66934444, compound

HRID 1365617Notes

Reaction equation

HRID 1365617 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[C:5](Cl)=[O:6])[CH3:2].[Cl:9][C:10]1[S:11][CH:12]=[CH:13][C:14]=1[Cl:15].[Al+3].[Cl-].[Cl-].[Cl-]>[N+](C)([O-])=O>[CH2:1]([O:3][C:4](=[O:8])[C:5]([C:12]1[S:11][C:10]([Cl:9])=[C:14]([Cl:15])[CH:13]=1)=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 140207Thiophene, 2,3-dichloro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 66934444HCID 66934444, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

At 5-10° C., Chloro-oxo-acetic acid ethyl ester (5.43 ml, 48.7 mmol) was added to 2,3-Dichlorothiophene (5 g, 32.6 mmol). A solution of AlCl3 (6.49 g, 48.7 mmol) dissolved in nitromethane (13 ml) was added dropwise such that the internal reaction temperature did not rise above 10° C. After 1 hour, the reaction mixture was poured into ice water and extracted with CH2Cl2 (2×100 ml). The organic layer was washed with 10% NaHCO3 (2×50 ml), water (1×50 ml) and brine (1×50 ml). Drying (Na2SO4) and concentration provided a light orange solid that was purified by silica gel chromatography (EtOAc/hexane-gradient) providing 6.8 g (82%) of the subtitle compound.

Workup

  1. additionwas added dropwise such that the internal reaction temperature
  2. customdid not rise above 10° C
  3. extractionextracted with CH2Cl2 (2×100 ml)
  4. washThe organic layer was washed with 10% NaHCO3 (2×50 ml), water (1×50 ml) and brine (1×50 ml)
  5. customDrying
  6. concentration(Na2SO4) and concentration
  7. customprovided a light orange solid
  8. customthat was purified by silica gel chromatography (EtOAc/hexane-gradient)

Sources & evidence

ORD record
ord-bed1b9df877e41e9ae7989bf5fee1a6d
Source dataset
uspto-grants-2011_02
Patent number
US07893051B2

Reaction notes

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