Acetic Acid → HCID 23291362, compound

HRID 365352Notes

Reaction equation

HRID 365352 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]2[O:11][CH2:12][O:13][C:8]2=[CH:7][C:4]=1[CH:5]=O.[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:17])[C:15](=[CH:5][C:4]1[CH:7]=[C:8]2[O:13][CH2:12][O:11][C:9]2=[CH:10][C:3]=1[O:2][CH3:1])[C:14]([O:22][CH2:23][CH3:24])=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 6018611,3-Benzodioxole-5-carboxaldehyde, 6-methoxy-

Product 1

HCID 23291362HCID 23291362, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the 2-methoxy-4,5-methylenedioxy benzaldehyde (16.0 g, 0.089 mol), diethyl malonate (15.0 ml, 0.090 mol), piperidine (4.4 ml, 0.044 mol) and acetic acid (2.5 ml, 0.045 mol) in benzene (75 ml) was stirred at reflux, equipped with a Dean-Stark apparatus, for 24 h. Upon removal of the solvent the crude residue was extracted with ethyl acetate and washed with 10% sodium carbonate solution, water, dried (Na2SO4). After removing the solvent, flash chromatography of the residue (silica gel, 25% ethyl acetate/hexane) provided the title compound as a yellow solid (26.0 g, 91%).

Workup

  1. temperatureat reflux
  2. customequipped with a Dean-Stark apparatus, for 24 h
  3. customUpon removal of the solvent the crude residue
  4. extractionwas extracted with ethyl acetate
  5. washwashed with 10% sodium carbonate solution, water
  6. dry with materialdried (Na2SO4)
  7. customAfter removing the solvent, flash chromatography of the residue (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3a585d2ba0bb497ebbf8b36f556cc21e
Source dataset
uspto-grants-2000_10
Patent number
US06127371

Reaction notes

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