4-Chlorobenzaldehyde → HCID 54088369, compound

HRID 2082287Notes

Reaction equation

HRID 2082287 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:15][O:14][C:13](=[O:16])[C:12]=2[C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:18])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1>N1CCCCC1.C(O)C>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[C:15]2[O:14][C:13](=[O:16])[C:12]([C:17]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[O:18])=[C:11]2[C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 54146329HCID 54146329, compound

Product 1

HCID 54088369HCID 54088369, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

4-(3,4-Dimethoxyphenyl)-2-oxo-2,5-dihydrofurane-3-carboxylic acid morpholide (1.00 g, 3 mmol) and 4-chlorobenzaldehyde (0.42 g, 3 mmol) were refluxed with ethanol (15 ml) and a small amount of piperidine (3 drops) for 3 h, then the reaction mixture was concentrated. The residue was dissolved in ethyl acetate (5 ml), petrol ether (2.5 ml) was added and the solution was applied onto a flash chromatography column (silica gel, 30 g). The column was eluted with ethyl acetate/petrol ether (2:1). The fractions containing the compound with the Rf (ethyl acetate/petrol ether, 2:1): 0.32 were collected and concentrated. 5-(4-Chlorobenzylidene)-4-(3,4-dimethoxyphenyl)-2-oxo-2,5-dihydro-furane-3-carboxylic acid morpholide was precipitated by addition of petrol ether.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (5 ml)
  3. additionpetrol ether (2.5 ml) was added
  4. washThe column was eluted with ethyl acetate/petrol ether (2:1)
  5. additionThe fractions containing the compound with the Rf (ethyl acetate/petrol ether, 2:1)
  6. custom0.32 were collected
  7. concentrationconcentrated
  8. custom5-(4-Chlorobenzylidene)-4-(3,4-dimethoxyphenyl)-2-oxo-2,5-dihydro-furane-3-carboxylic acid morpholide was precipitated by addition of petrol ether

Sources & evidence

ORD record
ord-66eab45166d14cb7953635a2b277686e
Source dataset
uspto-grants-1993_02
Patent number
US05189035

Reaction notes

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