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

HRID 83250

반응식

HRID 83250 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

HCID 28809765-Hydroxy-3-phenyl-5-(trifluoromethyl)-4,5-dihydroisoxazole수율 91.5%

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-f1bc98c06fe04b62b2e9262b0f153135
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846719B2

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