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

HRID 603406노트

반응식

HRID 603406 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: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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-35 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3eb75950c16b4c078b2e3427ec81429f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906653B2

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