Ethyl Acetate → HCID 14994871, compound

HRID 2248355Notes

Reaction equation

HRID 2248355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[C:13]([C:19]([O:21][CH3:22])=[O:20])#[C:14][C:15]([O:17][CH3:18])=[O:16].C(OCC)(=O)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[O:9][CH:10]([CH:11]=[CH:12]2)[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]3[C:19]([O:21][CH3:22])=[O:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12980Dimethyl acetylenedicarboxylateHCID 10965101HCID 10965101, compound

Product 1

HCID 14994871HCID 14994871, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(4-chlorophenyl)furan (prepared according to A.W. Johnson, J. of Chem. Soc. 1946, p 895-99) (0.105 g), and dimethyl acetylenedicarboxylate (0.07 mL) in distilled water (0.25 mL) was placed in a closed vial and subjected to ultrasonic vibration overnight. The reaction temperature at the end of the reaction was between 40 and 50° C. After cooling the Diels-Alder adduct was isolated by extraction with ethyl acetate. The ethyl acetate extract was dried (Na2SO4) and evaporated to dryness in-vacuo to provide almost pure product which was further purified by chromatography on silica gel using 5-10% acetone in n-hexane. The title compound (0.16 g) m.p. 84° C. was isolated from some of the combined fractions: PMR δH (CDCl3): 3.7(s,3H), 3.84 (s, 3H), 5.76 (d, 1H, J=1.2Hz), 7.58-7.29 (m, 5H).

Workup

  1. customwas between 40 and 50° C
  2. temperatureAfter cooling the Diels-Alder adduct
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated to dryness in-vacuo
  6. customto provide almost pure product which
  7. customwas further purified by chromatography on silica gel using 5-10% acetone in n-hexane

Sources & evidence

ORD record
ord-12fc22027c8a4d93bef1539defeace99
Source dataset
uspto-grants-1991_08
Patent number
US05039676

Reaction notes

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