2-Methylthiophene → Methyl 2-(5-methylthiophen-2-yl)-2-oxoacetate

HRID 1255093Notes

Reaction equation

HRID 1255093 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 55268432Methyl 2-(5-methylthiophen-2-yl)-2-oxoacetateYield 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. additionis slowly added
  2. washthe organic phase is washed with aq. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-4d4332800a7f4a93a720565766d70af2
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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