Diisopropylamine → ethyl 3-(diisopropylamino)-4,4-difluorobut-3-enoate

HRID 732269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732269
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].COP(O[C:15](=[C:22]([F:24])[F:23])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])(OC)=O>COC(C)(C)C>[CH:1]([N:4]([CH:5]([CH3:7])[CH3:6])[C:15](=[C:22]([F:24])[F:23])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 7912DiisopropylamineHCID 11492794Ethyl 3-[(dimethoxyphosphoryl)oxy]-4,4-difluorobut-3-enoate

Produkt 1

HCID 11528911ethyl 3-(diisopropylamino)-4,4-difluorobut-3-enoateAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

Diisopropylamine (15.2 g, 0.15 mol) is added dropwise over 10 min to a solution of ethyl 3-[(dimethoxyphosphoryl)oxy]-4,4-difluorobut-3-enoate (IV-1) (14.2 g, 97%, 0.05 mol) in 100 ml methyl-tert-butyl ether. After 19 h heating under reflux the reaction mixture is cooled to room temperature, washed twice with 10 ml 10% sodium chloride solution each time, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was distilled for further use. 8.8 g (95%, 67.4% of theory) of ethyl 3-(diisopropylamino)-4,4-difluorobut-3-enoate are obtained (boiling point 55-57° C. at 0.5 hPa).

Aufarbeitung

  1. temperatureAfter 19 h heating
  2. temperatureunder reflux the reaction mixture
  3. washwashed twice with 10 ml 10% sodium chloride solution each time
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. distillationThe residue was distilled for further use

Quellen und Nachweise

ORD-Eintrag
ord-385855a883774c868ae43bc64a47f5a5
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585998B2

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