Ethoxalyl chloride → HCID 66880855, compound

HRID 1844534Notes

Reaction equation

HRID 1844534 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:13][O:14][CH2:15][CH2:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH2:6]([O:5][C:3](=[O:4])[C:2]([C:21]1[CH:22]=[CH:23][C:18]([S:17][CH2:16][CH2:15][O:14][CH3:13])=[CH:19][CH:20]=1)=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 40561742-METHOXYETHYL PHENYL SULFIDEHCID 6451240Aluminum(III) Chloride

Product 1

HCID 66880855HCID 66880855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroglyoxylate (8.76 mL) was added dropwise to a suspension of aluminum chloride (13.2 g, crushed) in methylene chloride (127 mL) under stirring and cooling with ice, and (2-methoxyethyl)phenylsulfide (12.0 g) was added dropwise thereto. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water (200 mL), and the mixture was stirred for 10 minutes. The organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution (40 mL×3), and washed with saturated brine (60 mL). The washed organic layer was dried over anhydrous sodium sulfate, filtrated, and evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:1) to give 2-[4-(2-methoxyethylthio)phenyl]-2-oxoacetic acid ethyl ester (1.98 g).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. stirringthe mixture was stirred for 10 minutes
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous sodium hydrogen carbonate solution (40 mL×3)
  6. washwashed with saturated brine (60 mL)
  7. dry with materialThe washed organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltrated
  9. customevaporated under reduced pressure
  10. customThe obtained residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9a86842437eb420f9dabc433690f8d81
Source dataset
uspto-grants-2015_02
Patent number
US08946440B2

Reaction notes

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