4-Ethoxy-3,3'-difluoro-4'-propyl-[1,1'-biphenyl]-2,2'-dicarboaldehyde → 2-Ethoxy-1,8-difluoro-7-propyl-9,10-dihydrophenanthrene-9,10-diol

HRID 718486Notes

Reaction equation

HRID 718486 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:24])=[C:6]([CH:22]=[O:23])[C:7]([C:10]2[C:11]([CH:20]=[O:21])=[C:12]([F:19])[C:13]([CH2:16][CH2:17][CH3:18])=[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:19])[C:13]([CH2:16][CH2:17][CH3:18])=[CH:14][CH:15]=3)[CH:20]([OH:21])[CH:22]([OH:23])[C:6]=2[C:5]=1[F:24])[CH3:2]

Participants

5

Reactant 1

HCID 866960644-Ethoxy-3,3'-difluoro-4'-propyl-[1,1'-biphenyl]-2,2'-dicarboaldehyde

Product 1

HCID 680105352-Ethoxy-1,8-difluoro-7-propyl-9,10-dihydrophenanthrene-9,10-diolYield 59.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 3007855ZincchlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, zinc powder (0.295 g, 4.513 mmol) and zinc chloride (0.1 g, 0.752 mmol) were added to a DMF (5 mL) solution of compound (56) (0.5 g, 1.504 mmol), and the resultant mixture was agitated at 80° C. for 8 hours. The reaction mixture was quenched with 20 mL of 1N hydrochloric acid aqueous solution, and extracted with 10 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-propyl-9,10-dihydrophenanthrene-9,10-diol (57) (0.3 g, yield 59.7%) was obtained.

Workup

  1. customThe reaction mixture was quenched with 20 mL of 1N hydrochloric acid aqueous solution
  2. extractionextracted with 10 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-1cc4e4ef27074eef8edce61201498f49
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

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