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

HRID 1599513Notes

Reaction equation

HRID 1599513 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-53ea99193a3e4c8788b97e39e03f7dba
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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