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

HRID 545467Notes

Reaction equation

HRID 545467 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-cd9dbd9fbf09423a853aaf2912d92400
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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