Triethylamine → Ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid

HRID 1712267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712267
Cl[CH:2]([C:18]([O:20][CH3:21])=[O:19])[CH2:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16].[CH2:22](N(CC)CC)[CH3:23]>O1CCCC1>[CH2:22]([C:6]1[C:5]([N+:15]([O-:17])=[O:16])=[C:4]([CH:3]=[CH:2][C:18]([O:20][CH3:21])=[O:19])[CH:14]=[CH:13][C:7]=1[C:8]([OH:10])=[O:9])[CH3:23]

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 15091479Ethyl 4-(2-chloro-2-methoxycarbonylethyl)-3-nitrobenzoate

Produkt 1

HCID 68501280Ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The solution of 3.20 g of ethyl 4-(2-chloro-2-methoxycarbonylethyl)-3-nitrobenzoate in 130 ml of tetrahydrofuran is admixed with 6.46 ml of triethylamine and stirred at reflux over 18 hours. The reaction mixture is cooled, poured onto water (300 ml) and extracted with tert-butyl methyl ether (2×300 ml). The organic phases are washed successively with water (2×300 ml) and brine (150 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The crude title compound is obtained as a slightly yellowish solid from the residue. Rf=0.30 (1:2 EtOAc-heptane). Rt=4.50.

Aufarbeitung

  1. temperatureat reflux over 18 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water (300 ml)
  4. extractionextracted with tert-butyl methyl ether (2×300 ml)
  5. washThe organic phases are washed successively with water (2×300 ml) and brine (150 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-af588ccb59e74ceaafefe01be0891e3c
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790715B2

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