Potassium Hydroxide → 5-Nitro-6-(2,4-difluorophenylthio)-1-indanone ethylene ketal

HRID 1267810노트

반응식

HRID 1267810 반응식
[CH2:1]1[O:17][C:4]2([C:12]3[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10](Br)[CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[SH:26].[OH-].[K+]>N1C=CC=CC=1.O>[CH2:1]1[O:17][C:4]2([C:12]3[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10]([S:26][C:20]4[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=4[F:18])[CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 27370732,4-Difluorobenzene-1-thiolHCID 10357417HCID 10357417, 화합물

생성물 1

HCID 103167575-Nitro-6-(2,4-difluorophenylthio)-1-indanone ethylene ketal수율 81%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

To a mixture of 5-nitro-6-bromo-1-indanone ethylene ketal (600 mg, 2.0 mmol) and 2,4-difluorothiophenol (F. Klages and K. Bott Chem. Ber. 97,735 (1964)) (440 mg, 3.0 mmol) in pyridine (4.0 mL) was added a solution of 8M aqueous potassium hydroxide (375 μL, 3.0 mmol) at room temperature. The mixture was stirred for 2 h, diluted with water and extracted with ethyl acetate. The ethyl acetate extract was washed successively with 1M aqueous NaOH (2x),0.5M aqueous HCl (1x), brine, dried over anhydrous MgSO4 and concentrated in vacuo. Chromatography over silica gel and eluted with toluene: ethyl acetate (10:1) afforded the title compound (590 mg, 81%) as a pale yellow solid.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed successively with 1M aqueous NaOH (2x),0.5M aqueous HCl (1x), brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. washChromatography over silica gel and eluted with toluene: ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-733c2cb8f602483390d7489c6ce37321
출처 데이터셋
uspto-grants-2003_04
특허 번호
USRE038103E1

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