Propionic Acid → Ethyl 3-methyl-3-(trifluoromethyl)pent-4-enoate

HRID 425322

Reaktionsgleichung

Reaktionsgleichung von HRID 425322
[CH:1]([O:8]CC)([O:5][CH2:6][CH3:7])OCC.[F:11][C:12]([F:19])([F:18])[C:13]([CH3:17])=[CH:14][CH2:15]O.[C:20](O)(=O)CC>C(OCC)C>[CH3:17][C:13]([C:12]([F:19])([F:18])[F:11])([CH:14]=[CH2:15])[CH2:20][C:1]([O:5][CH2:6][CH3:7])=[O:8]

Komponenten

5

Edukt 3

HCID 1032Propionic AcidHCID 31214Ethyl orthoformateHCID 540431804,4,4-Trifluoro-3-methylbut-2-en-1-ol

Produkt 1

HCID 10910798Ethyl 3-methyl-3-(trifluoromethyl)pent-4-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

Triethyl orthoformate (6.51 mL, 35.7 mmol) was added to an ambient temperature mixture of 4,4,4-trifluoro-3-methylbut-2-en-1-ol (500 mg, 3.57 mmol) and propionic acid (13 μL, 0.18 mmol). After heating in a sealed tube at 200° C. for 30 h, the reaction mixture was cooled, diluted with diethyl ether and washed with saturated aqueous sodium bicarbonate. The organic phase was dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-20% ethyl acetate/hexane afforded ethyl 3-methyl-3-(trifluoromethyl)pent-4-enoate.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9b9a5bb07d734710b59aedda91ab7793
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106070B2

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