Iodine → 5-Chloro-3,3-diMethylindoline

HRID 1807865노트

반응식

HRID 1807865 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=O)[C:5]2([CH3:13])[CH3:12].[BH4-].[Na+].II.[Cl-].[NH4+]>O1CCCC1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][C:5]2([CH3:13])[CH3:12]

참가 물질

7

반응물 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 127000715-chloro-3,3-dimethyl-indolin-2-one

생성물 1

HCID 218361745-Chloro-3,3-diMethylindoline수율 82.1%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

To a solution of 630 mg of 5-chloro-3,3-dimethyl-1,3-dihydro-2H-indole-2-one in 6.30 mL of tetrahydrofuran was added 609 mg of sodium borohydride, followed by stirring for 10 minutes. Then, a solution of 1.63 g of iodine in 3.78 mL of tetrahydrofuran was added dropwise thereto at −10° C. or lower under cooling in an ice-acetone bath, followed by stirring at the same temperature for 30 minutes, then warming to room temperature, and stirring overnight. After diluting with chloroform, a saturated aqueous ammonium chloride solution was added dropwise thereto. The aqueous layer was separated and then the organic layer was washed with a saturated aqueous sodium sulfite solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 480 mg of 5-chloro-3,3-dimethylindoline as a colorless oily substance.

후처리

  1. stirringby stirring at the same temperature for 30 minutes
  2. temperaturewarming to room temperature
  3. stirringstirring overnight
  4. customThe aqueous layer was separated
  5. washthe organic layer was washed with a saturated aqueous sodium sulfite solution
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-c99cb78a62a54c9183b1f1c31c6515fd
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357688B2

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