Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-(5-methylthiophen-2-yl)prop-2-enoate

HRID 651634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 651634
[CH3:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12]>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:12])[CH:13]=[CH:7][C:5]1[S:6][C:2]([CH3:1])=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 616635-Methyl-2-thiophenecarboxaldehyde

Produkt 1

HCID 53641428Methyl 3-(5-methylthiophen-2-yl)prop-2-enoateAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 5-methyl-thiophene-2-carboxaldehyde (5 g, 40 mmol) in CH2Cl2 (100 mL) is added methyl (triphenylphosphoranylidene) acetate (13.3 g, 40 mmol). The solution is stirred for 72 hours. After this time, the solution is concentrated. The residue is slurried in Et2O. The solution is filtered through a bed of Celite. The collected liquid is concentrated. The residue is purified by column chromatography eluting with a gradient of 50% EtOAc/hexanes to 60% EtOAc/hexanes to give the title compound (4.5 g, 25 mmol) as an oil.

Aufarbeitung

  1. concentrationAfter this time, the solution is concentrated
  2. filtrationThe solution is filtered through a bed of Celite
  3. concentrationThe collected liquid is concentrated
  4. customThe residue is purified by column chromatography
  5. washeluting with a gradient of 50% EtOAc/hexanes to 60% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-997cf3b78b544914ba3c89f3e3fa0ad6
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281227B1

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