Dimethylformamide → 3-(1,3-dioxolan-2-yl)thiophene-2-carbaldehyde

HRID 1071627Notes

Reaction equation

HRID 1071627 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][CH:7]=1.C([Li])CCC.CN([CH:19]=[O:20])C.[Cl-].[NH4+]>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 3156302-(3-Thienyl)-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 115065723-(1,3-dioxolan-2-yl)thiophene-2-carbaldehydeYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

5.00 g (32.0 mmol) of 3-(1,3-dioxolan-2-yl)thiophene was dissolved in 100 ml of THF. 24.5 ml (1.5 mol/l) of n-butyllithium was added dropwise thereinto. After stirring for 0.5 hour, the mixture was cooled to −70° C., 3.10 ml (40.0 mmol) of DMF was added, and then the mixture was transferred to an ice bath. After stirring for about 2 hours, an aqueous saturated ammonium chloride was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give a crude product. The crude product was subjected to silica gel (ethyl acetate:hexane=1:2), to give 3.68 g (20.0 mmol, 62.4%) of the title compound as a yellow oil.

Workup

  1. customthe mixture was transferred to an ice bath
  2. stirringAfter stirring for about 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give a crude product

Sources & evidence

ORD record
ord-1d443a390ba649ef88ae65cb63f68d26
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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