Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl Benzofuran-3-acetate

HRID 368358

Reaktionsgleichung

Reaktionsgleichung von HRID 368358
[O:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=O)[CH2:2]1.[CH3:11][O:12][C:13](=[O:34])[CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13](=[O:34])[CH2:14][C:3]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[O:1][CH:2]=1

Komponenten

4

Edukt 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester2×HCID 23556Coumaranone

Produkt 1

HCID 10976279Methyl Benzofuran-3-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of 3-coumaranone (5.0 g, 37 mmol) and methyl(triphenylphosphoranylideneacetate) (13.5 g, 40 mmol) in toluene (70 mL) was heated to reflux for 25 hours. More toluene was added (50 mL), and after a further 5 hours, more methyl(triphenylphosphoranylideneacetate) (0.5 g, 1.5 mmol). After another 19 hours, a further 1.0 g (3.0 mmol) was added, and after a further 21 hours, the solvent was removed in vacuo. Column chromatography (heptane:ethyl acetate 4:1) gave the product as a brown oil, 33 mmol, 89%.

Aufarbeitung

  1. temperatureto reflux for 25 hours
  2. waitAfter another 19 hours
  3. additiona further 1.0 g (3.0 mmol) was added
  4. waitafter a further 21 hours
  5. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0b6ef6eb34264f15aaeb5f6505c82063
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133307

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