Water → 7-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

HRID 2235849

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HRID 2235849 반응식
O[C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[N:17][OH:18])[C:13]([F:16])([F:15])[F:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.O>C1COCC1.CCOC(C)=O>[F:16][C:13]([F:14])([F:15])[C:12]1[C:3]2[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=2[O:18][N:17]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 1363400761-(2,4-Dihydroxy-3-propylphenyl)-2,2,2-trifluoroethanone oxime

생성물 1

HCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol수율 50%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

1-(2,4-Dihydroxy-3-propylphenyl)-2,2,2-trifluoroethanone oxime (4.2 g, 15.96 mmol, prepared by the method described in WO9728137) and PPh3 (8.82 g, 33.6 mmol) were dissolved in THF (250 mL), and the mixture was cooled to 0° C. A solution of DEAD (5.02 mL, 32.0 mmol) in THF (150 mL) was slowly added over a period of 30 min. The reaction mixture was stirred for 1 h at 0° C. After addition of water (500 mL) and extraction with EtOAc (3×300 mL), the combined organic phases were washed with brine (300 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by silica gel flash chromatography (1:6 EtOAc/hexane) to yield 1.96 g (50%) of the title compound as a light yellow powder. 1H NMR (300 MHz, CDCl3): δ 1.00 (t, 3H), 1.73 (m, 2H), 2.88 (t, 2H), 5.34 (s, 1H), 6.93 (d, 1H), 7.48 (d, 1H).

후처리

  1. washthe combined organic phases were washed with brine (300 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by silica gel flash chromatography (1:6 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-57a297c6b25040cf9005196a91e21123
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714004B2

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