Boronic Acid → Ethyl 5,5,5-trifluoro-4-oxopentanoate

HRID 216685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216685
C(OC(=O)[CH:5]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])C.B(O)O>C(O)C>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH3:11]

Komponenten

4

Edukt 2

HCID 61668Boronic AcidHCID 11346247Butanedioic acid, (trifluoroacetyl)-, diethyl ester

Produkt 1

HCID 13379932Ethyl 5,5,5-trifluoro-4-oxopentanoateAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

In a one-necked round-bottomed flask equipped with a distillation head and cooler, a mixture of 2-(2,2,2-trifluoro-acetyl)-succinic acid diethyl ester (54.6 g, 202 mmol) and boronic acid (12.5 g, 202 mmol) is heated to 170° C. Heating is continued for4 h, during which time ethanol is gradually distilled off as it is formed. After cooling to room temperature, the reaction mixture is poured onto ice and extracted twice with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4 and concentrated at reduced pressure to afford a brown oil. The crude product is purified by distillation (60° C., 10 mbar) to afford the title compound as a colorless liquid (17.3 g, 87.3 mmol, 43%). 1H NMR (400 MHz, CDCl3, 298 K): δ=4.15 (q, J=7.1 Hz, 2H), 3.02 (t, J=6.4 Hz, 2H), 2.70 (t, J=6.4 Hz, 2H), 1.45 (t, J=7.1 Hz, 3H). MS (ES+): 199 (M(C7H9F3O3)+H)+.

Aufarbeitung

  1. customIn a one-necked round-bottomed flask equipped with a distillation head and cooler
  2. temperatureHeating
  3. distillationis gradually distilled off as it
  4. customis formed
  5. temperatureAfter cooling to room temperature
  6. additionthe reaction mixture is poured onto ice
  7. extractionextracted twice with EtOAc
  8. washThe combined organic layers are washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated at reduced pressure
  11. customto afford a brown oil
  12. distillationThe crude product is purified by distillation (60° C., 10 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-90be355142b34bdc87e73564076c5443
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193236B2

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