1,2-Dimethoxyethane → Methyl 3,3,3-tris(4-vinylphenyl)propionate

HRID 272083Notes

Reaction equation

HRID 272083 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:2]=1.Cl[C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:40]2[CH:45]=[CH:44][C:43](Cl)=[CH:42][CH:41]=2)([C:33]2[CH:38]=[CH:37][C:36](Cl)=[CH:35][CH:34]=2)[CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=1.[CH:47]([Sn](CCCC)(CCCC)CCCC)=[CH2:48].[F-].[K+].CO[CH2:66][CH2:67]OC>[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:1]([C:43]1[CH:42]=[CH:41][C:40]([C:27]([C:24]2[CH:23]=[CH:22][C:21]([CH:66]=[CH2:67])=[CH:26][CH:25]=2)([C:33]2[CH:34]=[CH:35][C:36]([CH:47]=[CH2:48])=[CH:37][CH:38]=2)[CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:45][CH:44]=1)=[CH2:2]

Participants

8

Reactant 5

HCID 80711,2-Dimethoxyethane3×HCID 11776Triphenylphosphine2×HCID 81998TributylvinyltinHCID 522689Potassium FluorideHCID 22647213HCID 22647213, compound

Product 1

HCID 22647215Methyl 3,3,3-tris(4-vinylphenyl)propionate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 86583787Diisobutylaluminumhydride tolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

The title compound was synthesized referring to Shirakawa, et al.'s method [J. Chem. Soc., Perkin Trans. 1, 2449-2450 (1997)]. To a solution of 71 mg of nickel (II)-acetylacetonate dihydrate and 289 mg of triphenylphosphine in 2 ml of 1,2-dimethoxyethane, 0.544 ml of 1.0 M diisobutylaluminium hydride-toluene solution was added at room temperature in nitrogen atmosphere, and the whole system was added to a solution of 364 mg of methyl 3,3,3-tris (4-chlorophenyl)-propionate and 1.01 g of vinyltributyltin in 5 ml of 1,2-dimethoxy-ethane at room temperature, followed by 22 hours' stirring at 80° C. Further, a system formed by adding 0.544 ml of 1.0 M diisobutyl-aluminum hydride-toluene solution to a solution of 71 mg of nickel (II)-acetylacetonate dihydrate and 289 mg of triphenylphosphine in 2 ml of 1,2-dimethoxyethane at room temperature in nitrogen atmosphere was added at room temperature, followed by 17 hours' stirring at 80° C. under heating. The reaction liquid was cooled to room temperature and 1N potassium fluoride was added, followed by 2 hours' stirring at room temperature. Filtering the reaction liquid through cerite, the filtrate was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the resulting residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=300/7—hexane/ethyl acetate=300/10) to provide 166 mg of the title compound.

Workup

  1. customThe title compound was synthesized
  2. customFurther, a system formed
  3. additionwas added at room temperature
  4. waitfollowed by 17 hours
  5. stirring' stirring at 80° C.
  6. temperatureunder heating
  7. customThe reaction liquid
  8. temperaturewas cooled to room temperature
  9. waitfollowed by 2 hours
  10. stirring' stirring at room temperature
  11. filtrationFiltering
  12. customthe reaction liquid through cerite, the filtrate
  13. washwashed successively with water and saturated brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. distillationDistilling the solvent off under reduced pressure
  16. customthe resulting residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=300/7—hexane/ethyl acetate=300/10)

Sources & evidence

ORD record
ord-01bb1174c77a4796a9d8f3fc79212660
Source dataset
uspto-grants-2008_11
Patent number
US07452908B2

Reaction notes

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