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

HRID 1267810ノート

反応式

HRID 1267810 の反応式
[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

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 27370732,4-Difluorobenzene-1-thiolHCID 10357417HCID 10357417、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-733c2cb8f602483390d7489c6ce37321
出典データセット
uspto-grants-2003_04
特許番号
USRE038103E1

反応ノート

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