Tert-Butyl nitrite → Methyl 5-phenylthiophene-3-carboxylate

HRID 590989

Reaction equation

HRID 590989 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15]>CN(C)C=O.O>[C:18]1([C:11]2[S:10][CH:9]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 705256Methyl 2-amino-5-phenylthiophene-3-carboxylate

Product 1

HCID 819151Methyl 5-phenylthiophene-3-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl nitrite (428 μL, 3.6 mmol) in N,N-dimethylformamide (5 mL) at 60° C. was dropwise added a solution of methyl 2-amino-5-phenylthiophene-3-carboxylate (11a) (420 mg, 1.8 mmol) in N,N-dimethylformamide (2.5 mL). The mixture was stirred at 60° C. for 1 hour, poured in water (15 mL) and extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (2×10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in toluene (5 mL) and concentrated in vacuo to provide the desired product (11b) (390 mg, 1.8 mmol, 99%) which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe organic layer was washed with brine (2×10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in toluene (5 mL)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9133882019c4cfa83115013489f40ff
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Linked notes

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