m-Chloroperbenzoic acid → Methyl thieno[3,4-b]thiophene-2-carboxylate

HRID 572904Notes

Reaction equation

HRID 572904 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH2:10][S:11][CH2:12][C:7]=2[CH:6]=1)=[O:4].C1C=C(Cl)C=C(C(OO)=O)C=1>C(OCC)(=O)C.C(=O)=O>[S:9]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]2=[CH:12][S:11][CH:10]=[C:8]12

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 3441857Methyl 4,6-dihydrothieno[3,4-b]thiophene-2-carboxylate

Product 1

HCID 19007653Methyl thieno[3,4-b]thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2.0 g (10 mmol) (3) in 30 mL ethyl acetate was stirred and cooled down in dry ice bath. MCPBA (1.75 g, 10 mmol) in 30 mL ethyl acetate was added dropwise to the reaction solution. After the addition, the mixture was kept stirring for overnight. Then the solvent was removed by evaporation and the residue contained a crude product of (4) and 3-chlorobenzoic acid.

Workup

  1. additionAfter the addition
  2. customThen the solvent was removed by evaporation

Sources & evidence

ORD record
ord-d05f430b1b2c4181be7bdca80667deae
Source dataset
uspto-grants-2015_05
Patent number
US09029499B2

Reaction notes

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