4-Ethoxy-3,3'-difluoro-4'-((4-propylcyclohexyl)methoxy)-[1,1'-biphenyl]-2,2'-dicarboaldehyde → 2-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-di hydrophenanthrene-9,10-diol

HRID 718490노트

반응식

HRID 718490 반응식
[CH2:1]([O:3][C:4]1[C:5]([F:32])=[C:6]([CH:30]=[O:31])[C:7]([C:10]2[C:11]([CH:28]=[O:29])=[C:12]([F:27])[C:13]([O:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19]3)=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)[CH3:2]>[Zn].[Cl-].[Zn+2].[Cl-].CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]2[C:10]3[C:11](=[C:12]([F:27])[C:13]([O:16][CH2:17][CH:18]4[CH2:19][CH2:20][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:22][CH2:23]4)=[CH:14][CH:15]=3)[CH:28]([OH:29])[CH:30]([OH:31])[C:6]=2[C:5]=1[F:32])[CH3:2]

참가 물질

5

반응물 1

HCID 866960654-Ethoxy-3,3'-difluoro-4'-((4-propylcyclohexyl)methoxy)-[1,1'-biphenyl]-2,2'-dicarboaldehyde

생성물 1

HCID 680105012-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-di hydrophenanthrene-9,10-diol수율 85.4%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 3007855Zincchloride촉매HCID 6228Dimethylformamide용매

실험 절차

Under a nitrogen atmosphere, zinc powder (1.85 g, 28.30 mmol) and zinc chloride (0.64 g, 4.696 mmol) were added to a DMF (50 mL) solution of compound (63) (4.20 g, 9.449 mmol), and the resultant mixture was agitated at 80° C. for 8 hours. The reaction mixture was quenched with 100 mL of 1N hydrochloric acid aqueous solution, and extracted with 50 mL of toluene 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 purified by silica gel column chromatography, and thus 2-ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-dihydrophenanthrene-9,10-diol (64) (3.6 g, yield 85.4%) was obtained.

후처리

  1. customThe reaction mixture was quenched with 100 mL of 1N hydrochloric acid aqueous solution
  2. extractionextracted with 50 mL of toluene three times
  3. washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationa solvent was distilled off by an evaporator
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-fca98a02fb6244f39b4a536129db3b34
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193908B2

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