Dimethylformamide → 1-Benzothiophene-2-carbaldehyde

HRID 1823645Notes

Reaction equation

HRID 1823645 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.CN([CH:18]=[O:19])C>C1COCC1>[S:1]1[C:2]([CH:18]=[O:19])=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7221Benzo(B)ThiopheneHCID 178418339Butyllithium

Product 1

HCID 7365001-Benzothiophene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of benzothiophene (2 g, 14.9 mmol) in 100 mL of THF cooled to −78° C. was added 1.6 M n-butyl lithium in hexanes (10.25 mL, 16.39 mmol). The mixture was stirred at −78° C. for 1 h, warmed to 0° C., stirred for 5 min, recooled to −78° C. and treated with DMF (4.62 mL, 59.61 mmol). The temperature was allowed to rise slowly overnight. The reaction was quenched with saturated aqueous ammonium chloride and extracted with diethyl ether. The combined organic extracts were washed with water and brine, dried over MgSO4 and concentrated to afford the title compound as an oil. (2.216 g, 91%).

Workup

  1. temperaturewarmed to 0° C.
  2. stirringstirred for 5 min
  3. customrecooled to −78° C.
  4. waitto rise slowly overnight
  5. customThe reaction was quenched with saturated aqueous ammonium chloride
  6. extractionextracted with diethyl ether
  7. washThe combined organic extracts were washed with water and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b068d3a540b7457392c328ce19a43eee
Source dataset
uspto-grants-2006_05
Patent number
US07038077B2

Reaction notes

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