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

HRID 619386Notes

Reaction equation

HRID 619386 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-6-al (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-3fa2c4e50f80405c98aa4b1344d611f8
Source dataset
uspto-grants-1999_09
Patent number
US05958968

Reaction notes

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