Sodium Hydroxide → 5-Hydroxy-3-phenyl-5-(trifluoromethyl)-4,5-dihydroisoxazole

HRID 332350

Reaktionsgleichung

Reaktionsgleichung von HRID 332350
[C:1]([CH2:9][C:10]([C:12]([F:15])([F:14])[F:13])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:17][OH:18].[OH-:19].[Na+]>>[C:2]1([C:1]2[CH2:9][C:10]([OH:19])([C:12]([F:13])([F:14])[F:15])[O:18][N:17]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedioneHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 28809765-Hydroxy-3-phenyl-5-(trifluoromethyl)-4,5-dihydroisoxazoleAusbeute 91,5 %

Versuchsvorschrift

Prepared according to J. Org. Chem., 1995, 60, 3907. A solution of benzoyltrifluoroacetone (21 g, 97 mmol) was added dropwise over 1 h, at 20-30° C., to a solution of hydroxylamine HCl (6.82 g, 98 mmol) containing sodium hydroxide (2 N, 51 mL, 102 mmol) and the resulting mixture heated under reflux for 45 min. After cooling to room temperature, the mixture was poured into ice-water (500 mL), the precipitate was filtered off, washed with water and dried under vacuum to afford the title compound (20.51 g, 91%) which was obtained as a white solid. MS: m/e=230.2 [M−H]−.

Aufarbeitung

  1. customPrepared
  2. temperaturethe resulting mixture heated
  3. temperatureunder reflux for 45 min
  4. filtrationthe precipitate was filtered off
  5. washwashed with water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5c703f0561004bd89096f0303a88a4e5
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877783B2

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