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

HRID 242764Notes

Reaction equation

HRID 242764 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-c57d31ad389d49c883de7ca97a887f21
Source dataset
uspto-grants-2014_02
Patent number
US08653228B2

Reaction notes

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