Dimethylformamide → 3-(Dimethoxymethyl)thiophene-2-carbaldehyde

HRID 1901777Notes

Reaction equation

HRID 1901777 reaction equation
[CH3:1][O:2][CH:3]([O:9][CH3:10])[C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.C([Li])CCC.CN(C)[CH:18]=[O:19]>O1CCCC1>[CH3:1][O:2][CH:3]([O:9][CH3:10])[C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:18]=[O:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 159181383-(Dimethoxymethyl)thiopheneHCID 178418339Butyllithium

Product 1

HCID 159181393-(Dimethoxymethyl)thiophene-2-carbaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-dimethoxymethylthiophene (14 g) in tetrahydrofuran (80 ml) was slowly added n-butyllithium (1.6M in n-hexane, 47.8 ml) at -10° C. with stirring. The reaction mixture was further stirred at same temperature for 1 hour. N,N-Dimethyl-formamide (11.9 g) in tetrahydrofuran (40 ml) was then added. The reaction mixture was warmed to room temperature and stirred for overnight. Ice water was added and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated to give brownish oily product (13 g, 80%).

Workup

  1. customat -10° C.
  2. stirringThe reaction mixture was further stirred at same temperature for 1 hour
  3. stirringstirred for overnight
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c81b3efb09dc45f78bd7b5e838f24806
Source dataset
uspto-grants-1996_11
Patent number
US05578636

Reaction notes

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