Water → Methyl 7-methoxy-1-benzothiophene-2-carboxylate

HRID 335554Notes

Reaction equation

HRID 335554 reaction equation
C(=O)([O-])[O-].[K+].[K+].[SH:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH3:13][O:14][C:15]1[C:16]([N+]([O-])=O)=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.O>CN(C=O)C>[CH3:13][O:14][C:15]1[C:16]2[S:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:18][C:17]=2[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 988673-Methoxy-2-nitrobenzaldehyde

Product 1

HCID 13123241Methyl 7-methoxy-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

550 mg (3.97 mmol) of potassium carbonate and 350 mg (3.31 mmol) of methyl mercaptoacetate are added to a solution of 600 mg (3.31 mmol) of 3-methoxy-2-nitrobenzaldehyde in 8 ml of DMF. The reaction mixture is heated at 70° C. for 4 h. After cooling, water is added. The resulting precipitate is filtered off, washed with water and dried under reduced pressure. This gives 387 mg (45.7% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-00a86039f3c1458a8248f2e29870bc58
Source dataset
uspto-grants-2014_11
Patent number
US08884017B2

Reaction notes

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