Ethyl Acetate → p-methylcarbonylstyrene

HRID 1244121Notes

Reaction equation

HRID 1244121 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1)=[O:3].[CH:11]([Sn](CCCC)(CCCC)CCCC)=[CH2:12].CCOC(C)=O>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>[CH:11]([C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1)=[CH2:12]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 81998Tributylvinyltin

Product 1

HCID 10909702p-methylcarbonylstyreneYield 101.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 521585Tris(furan-2-yl)phosphaneCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-iodoacetophenone (1.0 g, 4.1 mmol), Pd2(dba)3 (186 mg, 0.2 mmol), P(2-furyl)3 (94 mg, 0.4 mmol), and CuI (77 mg, 0.4 mmol) in 20 mL of anhydrous DMF under N2 atmosphere was added vinyltributyltin (1.43 mL, 4.9 mmol) via syringe. An exothermic reaction was observed. After stirred for over night at r.t., the reaction mixture was poured into EtOAc (20 mL), washed with sat. aq. CsF solution, and brine. The organic layer was dried over Na2SO4, evaporated. The titled compound (610 mg, 100%) was isolated after silica gel MPLC eluting with 0–15% EtOAC in hexanes.

Workup

  1. customAn exothermic reaction
  2. washwashed with sat. aq. CsF solution, and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-3819e07442814a6c8428cf236febba4e
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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