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

HRID 2090127Notes

Reaction equation

HRID 2090127 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-d13cef28273b45cbaea9509a10853449
Source dataset
uspto-grants-2013_05
Patent number
US08436134B2

Reaction notes

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