2-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-di hydrophenanthrene-9,10-diol → 2-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)phenanthrene-9,10-dione

HRID 718491ノート

反応式

HRID 718491 の反応式
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[C:10]([F:29])[C:11]([O:18][CH2:19][CH:20]4[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]4)=[CH:12][CH:13]=3)[CH:8]([OH:30])[CH:7]([OH:31])[C:6]=2[C:5]=1[F:32])[CH3:2]>CS(C)=O>[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[C:10]([F:29])[C:11]([O:18][CH2:19][CH:20]4[CH2:21][CH2:22][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:24][CH2:25]4)=[CH:12][CH:13]=3)[C:8](=[O:30])[C:7](=[O:31])[C:6]=2[C:5]=1[F:32])[CH3:2]

参加物

3

反応物 1

HCID 680105012-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-di hydrophenanthrene-9,10-diol

生成物 1

HCID 680104992-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)phenanthrene-9,10-dione収率 89.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

IBX (9.03 g, 32.25 mmol) was added to 100 mL of DMSO, the resultant mixture was agitated at room temperature for 30 minutes, and then compound (64) (3.6 g, 8.062 mmol) was added thereto, and the resultant mixture was further agitated for 3 hours. The reaction mixture was filtered, 200 mL of water was added to a filtrate, and the resultant mixture was extracted with 100 mL of ethyl acetate three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was recrystallized from toluene, and thus 2-ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)phenanthrene-9,10-dione (65) (3.2 g, yield 34.5%) was obtained.

後処理

  1. filtrationThe reaction mixture was filtered
  2. addition200 mL of water was added to a filtrate
  3. extractionthe resultant mixture was extracted with 100 mL of ethyl acetate three times
  4. washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationa solvent was distilled off by an evaporator
  7. customThe residue was recrystallized from toluene

出典と根拠

ORDレコード
ord-3cc4134c30a94f808c262269332f5fe1
出典データセット
uspto-grants-2015_11
特許番号
US09193908B2

反応ノート

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