Acetic Acid → HCID 22993835, compound

HRID 1857568Notes

Reaction equation

HRID 1857568 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]=1C=O.[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].N1CCCC[CH2:26]1.C(O)(=O)C>C1C=CC=CC=1>[CH2:12]1[O:11][C:9]2[C:8](=[CH:7][CH2:4][C:3]([O:2][CH3:1])([CH:10]=2)[CH:26]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:22][CH2:23][CH3:24])=[O:21])[O:13]1

Participants

6

Reactant 4

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

Product 1

HCID 22993835HCID 22993835, compoundYield 182.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the 2-methoxy-4,5-methylenedioxy benzaldehyde (16.00 g, 0.089 mol), diethyl malonate (15.00 mL, 0.090 mol), piperidine (4.40 mL, 0.044 mol) and acetic acid (2.50 mL, 0.045 mol) in benzene (75 mL) 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 (26.00 g, 91%): 1H NMR (250 MHz, CDCl3) δ 8.50 (s, 1H), 7.45 (d, J=10 Hz, 1H), 7.10 (d, J=15 Hz, 1H), 5.85 (s, 2H), 4.15 (q, 4H), 3.40 (s, 3H), 1.20 (m, 6H); mp: 118° C.

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-b213342a18854eba8e37a8048f54b41d
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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