Dimethylformamide → 5-(4-Fluorophenoxy)-2-thiophenecarboxaldehyde

HRID 2082093Notes

Reaction equation

HRID 2082093 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:21]=[O:22]>C1COCC1>[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][C:7]2[S:8][C:9]([CH:21]=[O:22])=[CH:10][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 197795412-(4-Fluorophenoxy)thiopheneHCID 178418339Butyllithium

Product 1

HCID 194222425-(4-Fluorophenoxy)-2-thiophenecarboxaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-fluorophenoxy)thiophene (3.66 g, 18.9 mmol) in THF (90 mL) at -78° C., was added butyllithium (7.5 ml of a 2.5M solution in hexanes, 18.9 mmol) dropwise. Upon completion of addition, the mixture was stirred for 20 min. N,N-Dimethylformamide (1.52 g, 20.8 mmol) was then added and the reaction was stirred for 40 min at -78° C. It was then quenched with saturated aqueous NH4Cl (100 mL) and extracted with ethyl acetate (3×100 mL). The organics were combined, dried over MgSO4 and concentrated. The resulting residue was chromatographed (silica gel; 3:1 hexanes, ether) to afford 3.59 g (86%) of 5-(4-fluorophenoxy)-2-thiophenecarboxaldehyde as a slightly orange solid.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction was stirred for 40 min at -78° C
  3. customIt was then quenched with saturated aqueous NH4Cl (100 mL)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting residue was chromatographed (silica gel; 3:1 hexanes, ether)

Sources & evidence

ORD record
ord-fede4073823c4587a98d7cbbc0616e4d
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

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