(Diethylamino)sulfur trifluoride → 3-Methyl-7-propyl-1,2-benzisoxazol-6-ol

HRID 603406ノート

反応式

HRID 603406 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:14][OH:15])[CH3:13].C(N(S(F)(F)F)CC)C>C(Cl)Cl>[CH3:13][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:15][N:14]=1

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 1363886031-(2,4-Dihydroxy-3-propylphenyl)ethanone oxime

生成物 1

HCID 1360297883-Methyl-7-propyl-1,2-benzisoxazol-6-ol収率 77.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-35 °C

実験手順

1-(2,4-dihydroxy-3-propylphenyl)ethanone oxime (400 mg, 1.91 mmol) (Example 66) was dissolved in CH2Cl2 and the solution was cooled to −35° C. under an atmosphere of argon. (Diethylamino)sulfur trifluoride (DAST) (647 mg, 4.01 mmol) was added dropwise and the solution was allowed to warm to −25° C. over 2 h. The mixture was quenched with NaHCO3 (saturated aqueous solution). The organic phase separated and the aqueous phase extracted with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:3) gave 282 mg (77%) of the title compound as a faintly red-colored solid. 1H NMR (400 MHz, CDCl3): δ 0.95 (t, 3H), 1.67 (m, 2H), 2.56 (s, 3H), 2.79 (t, 2H), 6.76 (d, 1H), 7.19 (d, 1H).

後処理

  1. temperatureto warm to −25° C. over 2 h
  2. customThe mixture was quenched with NaHCO3 (saturated aqueous solution)
  3. customThe organic phase separated
  4. extractionthe aqueous phase extracted with CH2Cl2
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v)=1:3)

出典と根拠

ORDレコード
ord-3eb75950c16b4c078b2e3427ec81429f
出典データセット
uspto-grants-2011_03
特許番号
US07906653B2

反応ノート

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