2-Methylthiophene → HCID 55268432, compound

HRID 77060

Reaction equation

HRID 77060 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].Cl[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8].[CH3:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1>C(Cl)Cl>[CH3:10][O:9][C:7](=[O:8])[C:6]([C:15]1[S:14][C:13]([CH3:12])=[CH:17][CH:16]=1)=[O:11]

Participants

5

Reactant 3

HCID 111262-MethylthiopheneHCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 55268432HCID 55268432, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of aluminum trichloride (2.75 g, 20.6 mmol) and methyl 2-chloro-2-oxoacetate (1.90 mL, 20.7 mmol) in dry DCM (25 mL), cooled at 0° C. and under nitrogen atmosphere, is added 2-methylthiophene (1.00 mL, 10.33 mmol) dropwise. The reaction is stirred at RT for 15 hours. Then the mixture is cooled at 0° C., ice-water is slowly added and the organic phase is washed with aq. NaHCO3 and brine, dried over Na2SO4 and evaporated to obtain intermediate I266 as a brown oil (1.9 g, quantitative yield).

Workup

  1. temperatureThen the mixture is cooled at 0° C.
  2. washthe organic phase is washed with aq. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-7c5d0a31ffa3492c9161eb21654422d0
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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