Dimethylformamide → Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoate

HRID 29116

Reaktionsgleichung

Reaktionsgleichung von HRID 29116
CN(C)C=O.CC(C)([O-])C.[Na+].[CH3:12][CH2:13][O:14][C:15]([CH:17](P(OCC)(OCC)=O)[CH3:18])=[O:16].[CH3:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1>O>[CH3:18][C:17](=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([CH3:27])=[CH:29][CH:30]=1)[C:15]([O:14][CH2:13][CH3:12])=[O:16]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 77254-MethylbenzaldehydeHCID 107155Triethyl 2-phosphonopropionateHCID 23676156Sodium t-butoxide

Produkt 1

HCID 68712312Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoateAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-2.5 °C

Versuchsvorschrift

To dimethylformamide (1802 ml) that had been cooled to −10° C. was added sodium tert-butoxide (528.6 g) and the solution was stirred at −5 to 0° C. for 30 min. Triethyl 2-phosphonopropionate (1310 g) was added dropwise thereto at 10° C. or below. The solution was stirred at 2 to 5° C. for 1 hr, and 4-methylbenzaldehyde (600.8 g) was added dropwise thereto at 10° C. or below and the solution was stirred at room temperature for 1 hr. Water was added thereto and the solution was extracted with toluene. The extract was washed with water and the solvent was distilled off to give the title compound as an oil (1009 g, yield 98.8%).

Aufarbeitung

  1. customat 10° C. or below
  2. stirringThe solution was stirred at 2 to 5° C. for 1 hr
  3. stirringat 10° C. or below and the solution was stirred at room temperature for 1 hr
  4. extractionthe solution was extracted with toluene
  5. washThe extract was washed with water
  6. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-2eb2a4dd9a0740a3b26f8005a0b593f5
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420070B2

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