Sulfuric Acid → HCID 15035299, compound

HRID 1681289Notes

Reaction equation

HRID 1681289 reaction equation
CO[CH:3]([O:22]C)[C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:9]([O:20][CH3:21])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.C([Li])CCC.CN(C)[CH:31]=[O:32].S(=O)(=O)(O)O>O1CCCC1.CCCCCC>[CH3:21][O:20][CH:9]([C:5]1[S:6][C:7]([CH:31]=[O:32])=[CH:8][C:4]=1[CH:3]=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 14988608HCID 14988608, compoundHCID 178418339Butyllithium

Product 1

HCID 15035299HCID 15035299, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-30 °C

Procedure

16.9 g of 3-dimethoxymethyl-2-(α-methoxy-3,4-dimethoxybenzyl)thiophene are dissolved in 200 ml of tetrahydrofuran. 37.5 ml of 1.6M n-butyl lithium in hexane are added dropwise thereto at -78° C., and the reaction mixture is warmed up to -30° C. gradually. After the mixture is chilled at -78° C., 4.3 ml of N,N-dimethylformamide are added thereto. The mixture is stirred for 30 minutes. The reaction mixture is warmed up to ambient temperature. The mixture is acidified with diluted sulfuric acid, stirred for one hour and extracted with chloroform. The extract is washed with aqueous sodium bicarbonate solution and water, dried and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography [solvent: hexane-ethyl acetate (2:1)], and the eluate is condensed. 14.6 g of 2-(α-methoxy-3,4-dimethoxybenzyl)thiophen-3,5-dicarbaldehyde are obtained as an oil.

Workup

  1. temperatureAfter the mixture is chilled at -78° C.
  2. temperatureThe reaction mixture is warmed up to ambient temperature
  3. stirringstirred for one hour
  4. extractionextracted with chloroform
  5. washThe extract is washed with aqueous sodium bicarbonate solution and water
  6. customdried
  7. customevaporated under reduced pressure
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography [solvent: hexane-ethyl acetate (2:1)]
  10. customcondensed

Sources & evidence

ORD record
ord-3cd4e302adee432fafb8f6688c04a81f
Source dataset
uspto-grants-1992_12
Patent number
US05169861

Reaction notes

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