Potassium Carbonate → Ethyl 3-ethynyl-6-nitro-1-benzothiophene-2-carboxylate

HRID 43799Notes

Reaction equation

HRID 43799 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]2[C:8]([C:16]#[C:17][Si](C)(C)C)=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C1COCC1>[C:16]([C:8]1[C:7]2[CH:22]=[CH:23][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[S:10][C:9]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[CH:17]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67549085Ethyl 6-nitro-3-[(trimethylsilyl)ethynyl]-1-benzothiophene-2-carboxylate

Product 1

HCID 86648747Ethyl 3-ethynyl-6-nitro-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 6-nitro-3-[(trimethylsilyl)ethynyl]-1-benzothiophene-2-carboxylate obtained in Example (183c) (110 mg, 0.32 mmol) was dissolved in ethanol (8 mL) and THF (8 ml). Potassium carbonate (13 mg, 0.1 mmol) was added, and the mixture was stirred at room temperature for four hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate) to obtain the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-b698e8162275484c9d0d194fc25305e0
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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