Acetic Acid → Diethyl 2-(5-methoxy-2,3-dihydrobenzofuran-6-yliden)-malonate

HRID 1740514Notes

Reaction equation

HRID 1740514 reaction equation
[CH3:1][O:2][C:3]1[C:4](C=O)=[CH:5][C:6]2[O:10][CH2:9][CH2:8][C:7]=2[CH:11]=1.[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.O>[CH3:1][O:2][CH:3]1[CH:11]=[C:7]2[CH2:8][CH2:9][O:10][C:6]2=[CH:5][C:4]1=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:22][CH2:23][CH3:24])=[O:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 100124745-Methoxy-2,3-dihydrobenzofuran-6-carbaldehyde

Product 1

HCID 69543719Diethyl 2-(5-methoxy-2,3-dihydrobenzofuran-6-yliden)-malonate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 5-Methoxy-2,3-dihydrobenzofuran-6al (295 mg, 1.66 mmol) in benzene was added diethyl malonate (265 mg, 1.66 mmol), acetic acid (20 mL, 0.35 mmol) and piperidine (30 mL, 0.30 mmol). The mixture was heated at reflux for 3 h and then poured into 100 mL of water. This mixture was extracted with three 50 mL portion of ethyl acetate. The combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave quatitative yield of the title compound as a yellowish oil: 1H NMR (400 MHz, CDCl3) d 8.02 (s, 1H), 6.79 (s, 1H), 6.78 (s, 1H), 4.52 (t, 2H), 4.30 (m, 4H), 3.80 (s, 3H), 3.18 (t, 2H), 1.28 (m, 6H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. extractionThis mixture was extracted with three 50 mL portion of ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-cb8dc08f70e9416380ddd6e7d9b0fcd5
Source dataset
uspto-grants-1999_10
Patent number
US05969151

Reaction notes

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