Potassium Carbonate → Dimethyl benzo[b]thiophene-2,6-dicarboxylate

HRID 1172844Notes

Reaction equation

HRID 1172844 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+]([O-])=O)=O.C([O-])([O-])=O.[K+].[K+].[C:22]([O:26][CH3:27])(=[O:25])[CH2:23][SH:24]>CN(C=O)C>[CH3:27][O:26][C:22]([C:23]1[S:24][C:4]2[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=[CH:12][C:3]=2[CH:1]=1)=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 3457222Methyl 4-formyl-3-nitrobenzoate

Product 1

HCID 59556411Dimethyl benzo[b]thiophene-2,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 4-formyl-3-nitrobenzoate (6.68 g, 31.9 mmol) and K2CO3 (5.55 g, 38.3 mmol) in DMF (70 mL) was slowly added methyl thioglycolate (2.91 mL, 31.9 mmol). The mixture was stirred at RT for 1 h, then at 50° C. for 24 h. The resultant mixture was poured into H2O/ice and stirred until a precipitate formed. The green solid was filtered. 1H NMR (DMSO-d6) δ 8.72 (s, 1H), 8.25 (s, 1H), 8.12 (d, J=8.0 Hz), 7.95 (d, J=8.0 Hz), 3.87 (s, 6H). MS (EI): cal'd (MH+) 251.03, exp (MH+) 251.18.

Workup

  1. waitat 50° C. for 24 h
  2. stirringstirred until a precipitate
  3. customformed
  4. filtrationThe green solid was filtered

Sources & evidence

ORD record
ord-3d3955e7c9104135bdad99acac74278d
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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