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

HRID 603378

反応式

HRID 603378 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-83ffd2f5ab7c4aedbb33add5f1d566ba
出典データセット
uspto-grants-2011_03
特許番号
US07906653B2

関連ノート

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