Potassium Fluoride → HCID 59396515, compound

HRID 2383042Notes

Reaction equation

HRID 2383042 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]=[C:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:23]([O:25]CC)=[CH2:24])CCC.[F-].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]1([C:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([C:23](=[O:25])[CH3:24])[CH:11]=3)[CH2:6][CH2:7][N:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-2×HCID 67538221HCID 67538221, compound

Product 1

HCID 59396515HCID 59396515, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

7-bromo-1-cyclohexyl-3,4-dihydroisoquinoline (4.01 g) was dissolved in 1,4-dioxane (100 mL), to which tributyl(1-ethoxyvinyl)tin (7.43 g), potassium fluoride (2.39 g), and tetrakis(triphenylphosphine)palladium (1.58 g) were then added, followed by stirring at 80° C. for 5 hours. Thereafter, to the reaction liquid were further added tributyl(1-ethoxyvinyl)tin (2.47 g) and tetrakis(triphenylphosphine)palladium (1.58 g), followed by stirring for 14 hours. Then, the reaction liquid was filtered through celite and the insoluble materials were separated. 4 M HCl/dioxane (20 mL) was added to the insoluble materials, followed by stirring at 60° C. for 30 minutes. The solvent was evaporated and water was added to the mixture which was then extracted with EtOAc. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain 1-(1-cyclohexyl-3,4-dihydroisoquinolin-7-yl)ethanone (2.24 g).

Workup

  1. additionwere then added
  2. customThereafter, to the reaction liquid
  3. stirringby stirring for 14 hours
  4. customThen, the reaction liquid
  5. filtrationwas filtered through celite
  6. customthe insoluble materials were separated
  7. addition4 M HCl/dioxane (20 mL) was added to the insoluble materials
  8. stirringby stirring at 60° C. for 30 minutes
  9. customThe solvent was evaporated
  10. additionwater was added to the mixture which
  11. extractionwas then extracted with EtOAc
  12. washThe extract was washed with saturated brine
  13. dry with materialdried over magnesium sulfate
  14. customThe solvent was evaporated
  15. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record
ord-32b86e758cb64827adf12c1e9d297da5
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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