4-Fluorobenzaldehyde → Ethyl 3-(4-fluorophenyl)prop-2-enoate

HRID 582550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582550
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13][CH3:14])=[O:11]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:15][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 680234-FluorobenzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Produkt 1

HCID 367200Ethyl 3-(4-fluorophenyl)prop-2-enoateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 4-fluorobenzaldehyde (8.6 mL, 0.081 mol) and carboethoxymethylene triphenylphosphorane (34 g, 0.097 mol) in toluene (400 mL) was heated at reflux for 3 h. After this time the solvent was removed in vacuo and the residue triturated in petrol:Et2O (1:1). The mixture was filtered and the filtrate evaporated. The residue was chromatographed on silica gel, eluting with petrol:Et2O (3:1), to afford the ester (14.4 g, 92%) as a low-melting colourless solid. 1H NMR (major isomer) (250 MHz, CDCl3) δ1.34 (3H, t, J=7.0 Hz), 4.26 (2H, q, J=7.0 Hz), 6.36 (1H, d, J=16 Hz), 7.07 (2H, dd, JHA-HB =8.6 Hz and JHA-F =8.6 Hz), 7.51 (2H, dd, JHB-HA =8.6 Hz and JHB-F =5.3 Hz), 7.65 (1H, d, J=16 Hz).

Aufarbeitung

  1. temperatureat reflux for 3 h
  2. customAfter this time the solvent was removed in vacuo
  3. customthe residue triturated in petrol:Et2O (1:1)
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with petrol:Et2O (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-2ce14e44719246ae944f1a6520d62db3
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925638

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