HCID 21584088、化合物 → HCID 21584080、化合物

HRID 583031ノート

反応式

HRID 583031 の反応式
[C:1]1([S:7][C:8]2([O:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=3[N+:23]([O-])=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O.C(O)(=O)C.[Fe]>[C:1]1([S:7][C:8]2([O:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:20])([F:21])[F:22])=[CH:14][C:13]=3[NH2:23])[CH2:9][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 1

HCID 21584088HCID 21584088、化合物

生成物 1

HCID 21584080HCID 21584080、化合物収率 78%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

Iron powder (13.5 g, 241 mmol) was added to a suspension of 2-(1-phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)nitrobenzene (Description 4, 11.27 g, 30.1 mmol) in water (300 mL) and acetic acid (75 mL) and the mixture was stirred at 80° C. overnight. The mixture was cooled and filtered through celite, washing with ether. The filtrate was extracted with ether, the combined organic fractions were washed with aqueous sodium hydroxide (1M), dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (90:10 increasing to 80:20), to give the title compound as a yellow solid (8 g, 78%). 1H NMR (360 MHz, CDCl3) δ7.48 (2 H, m), 7.34-7.23 (3 H, m), 7.15 (1 H, d, J 8.74 Hz), 6.60-6.56 (2 H, m), 3.78 (2 H, br s), 1.49-1.46 (2 H, m), and 1.39-1.35 (2 H, m).

後処理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. washwashing with ether
  4. extractionThe filtrate was extracted with ether
  5. washthe combined organic fractions were washed with aqueous sodium hydroxide (1M)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with hexane/Et2O (90:10 increasing to 80:20)

出典と根拠

ORDレコード
ord-c5e4c3751384441ca00a4d06307ab623
出典データセット
uspto-grants-1999_07
特許番号
US05929054

反応ノート

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