Ethyl Acetate → Ethyl 3-(3-fluoro-4-methyloxyphenyl)Acrylate

HRID 984701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984701
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.C(OP([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(OCC)=O)C.[H-].[Na+].C(OCC)(=O)C>C(OCCOCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 676963-Fluoro-p-anisaldehyde

Produkt 1

HCID 53705486Ethyl 3-(3-fluoro-4-methyloxyphenyl)Acrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12375Ethylene glycol diethyl etherLösungsmittel

Versuchsvorschrift

A solution of 3-fluoro-4-methoxybenzaldehyde (2.20 g, Ald) in 1,2-diethoxyethane (5 ml) was added with ethyl diethylphosphonoacetate (3.12 ml, TCI) and then added with 60% sodium hydride (624 mg) under ice cooling. The reaction mixture was stirred for 10 minutes, then warmed to room temperature and stirred for 5 hours. The reaction mixture was added with ethyl acetate (90 ml) and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 17, 3.16 g).

Aufarbeitung

  1. stirringstirred for 5 hours
  2. washwashed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine
  3. customThe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography (Quad, hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-7129751fbb23496b8aba08e4f7883404
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867320B2

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