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Water → Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate

HRID 520739
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 520739
C1CC1.[CH2:4]([O:6][C:7]([CH:9]1[CH2:11][C:10]1([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH3:5].[N:24]([O-])=[O:25].[Na+].O>C(C(O)=O)(F)(F)F>[CH2:4]([O:6][C:7]([C:9]1[CH2:11][C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:25][N:24]=1)=[O:8])[CH3:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6351CyclopropaneHCID 11300104HCID 11300104, VerbindungHCID 23668193Sodium Nitrite

Produkt 1

HCID 6451155Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422
Trifluoroacetic acid
Lösungsmittel

Reaktionsbedingungen

Temperatur
18 °C

Versuchsvorschrift

The cyclopropane derivative, 2,2-diphenylcyclopropanyl carboxylate ethyl ester (0.97 g, 3.7 mmol) was dissolved in 3.7 mL CF3CO2H. Into the solution was added NaNO2 (0.28 g, 4.0 mmol, 1.1 eq.) in several ports so that the reaction temperature did not excess 40° C. After addition, the reactants were stirred at room temperature (about 18° C.) for half an hour. And the reactants were poured into an iced water and extracted with diethyl ether (2×20 mL); the ethereal solutions were combined and subsequently washed with sat. NaHCO3 (2*20 mL), then water (20 mL) and brine (20 mL). The washed ethereal solution was then dried over anhydrous Na2SO4. After removing the desiccant, the ethereal solution was concentrated to obtain a light brown oil. The crude product 1H NMR of the crude product showed that the reaction was clean and a virtual 100% yield. The crude product was further purified over silica chromatography (Rf: 0.45, eluent: 20% ethyl acetate in petrol) to obtain 5,5-diphenylisoxazoline carboxylate ethyl ester 0.958 g (89% yield) as a white solid. 1H NMR (400 MHz, CDCl3): 7.41-7.26 (10H, m), 4.34 (2H, q, J=7.1 Hz), 3.86 (2H, s), 1.36 (3H, t, J=7.1 Hz). 13C NMR (400 MHz, CDCl3): 160.54, 151.09, 142.99, 128.54, 128.02, 125.95, 94.79, 62.15, 46.78, 14.12.

Aufarbeitung

  1. customdid not excess 40° C
  2. additionAfter addition
  3. extractionextracted with diethyl ether (2×20 mL)
  4. washsubsequently washed with sat. NaHCO3 (2*20 mL)
  5. dry with materialThe washed ethereal solution was then dried over anhydrous Na2SO4
  6. customAfter removing the desiccant
  7. concentrationthe ethereal solution was concentrated
  8. customto obtain a light brown oil
  9. customThe crude product was further purified over silica chromatography (Rf: 0.45, eluent: 20% ethyl acetate in petrol)

Quellen und Nachweise

ORD-Eintrag
ord-ec5abfb773e34ac49556534468e396c0
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09328074B2

Notizen zur Reaktion

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