Tributylvinyltin → HCID 17861984, compound

HRID 1785358Notes

Reaction equation

HRID 1785358 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([O:13][C:14](=[O:18])[N:15]([CH3:17])[CH3:16])[CH:10]=[CH:9][C:8]=1[CH:19]=[O:20])(=O)=O.[Cl-].[Li+].[CH2:25]([Sn](CCCC)(CCCC)C=C)[CH2:26]CC.[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.C(C1C=CC=C(C(C)(C)C)C=1O)(C)(C)C>[CH3:16][N:15]([CH3:17])[C:14](=[O:18])[O:13][C:11]1[CH:10]=[CH:9][C:8]([CH:19]=[O:20])=[C:7]([CH:25]=[CH2:26])[CH:12]=1

Participants

8

Reactant 4

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 17861973HCID 17861973, compound

Product 1

HCID 17861984HCID 17861984, compoundYield 79.5%

Reagents, catalysts & solvents 3

HCID 314052,6-Di-tert-butylphenolCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-dimethylcarbamoyloxy-2-formyl-phenyl trifluoromethanesulfonate (4.13 g, 12.1 mmol) obtained in step (b) of Example 192 in 1,4-dioxane (15 ml) were added tetrakis(triphenylphosphine)palladium (693 mg, 0.600 mmol), 2,6-di-t-butylphenol (5 mg), lithium chloride (1.54 g, 36.4 mmol) and tributyl(vinyl)tin (4.23 ml, 14.5 mmol) with stirring, and the resulting mixture was stirred for 3 hours at 100° C. under a nitrogen atmosphere. Subsequently, saturated aqueous potassium fluoride solution (5 ml) was added to the reaction mixture, and the resulting mixture was stirred for 2 hours at room temperature, filtered, and evaporated in vacuo. To the residue was added water (40 ml), and the resulting mixture was extracted with ethyl acetate (50 ml×2). The organic layer was washed successively with 1N hydrochloric acid (40 ml×1) and saturated aqueous sodium chloride solution (40 ml×1), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (10:1-1:1) as the eluent to afford the title compound (2.11 g, yield: 79%) as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred for 3 hours at 100° C. under a nitrogen atmosphere
  2. stirringthe resulting mixture was stirred for 2 hours at room temperature
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. additionTo the residue was added water (40 ml)
  6. extractionthe resulting mixture was extracted with ethyl acetate (50 ml×2)
  7. washThe organic layer was washed successively with 1N hydrochloric acid (40 ml×1) and saturated aqueous sodium chloride solution (40 ml×1)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customto afford the crude product
  12. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2dbee7a0197c46ba8a7ac5f01fbb9607
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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