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 718490Notes

Reaction equation

HRID 718490 reaction equation
[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]

Participants

5

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 3007855ZincchlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fca98a02fb6244f39b4a536129db3b34
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

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