N-methyl-2-pyrrolidone → Methyl 4-(prop-2-enyl)-2-(2-methylphenyl)benzoate

HRID 383132Notes

Reaction equation

HRID 383132 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:3]=1.[CH2:19]([Sn](CCCC)(CCCC)CCCC)[CH:20]=[CH2:21].CN1C(=O)CCC1>C1(C)C=CC=CC=1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:21]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:3]=1)[CH:20]=[CH2:19]

Participants

7

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 90628AllyltributylstannaneHCID 11508596HCID 11508596, compound

Product 1

HCID 18361425Methyl 4-(prop-2-enyl)-2-(2-methylphenyl)benzoateYield 74%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-iodo-2-(2-methylphenyl)benzoate (10.0 g, 28.4 mmol), allyltributyl tin (11.3 g, 34.1 mmol), and dichlorobis(triphenylphosphine)palladium (II) (1.0 g, 1.42 mmol) were combined in 50 mL toluene and 20 mL NMP and heated at 125° C. for 18 hours. The reaction was diluted with EtOAc, washed with water and brine, dried over Na2SO4, and chromatographed (5% EtOAc in hexanes) to provide the title compound in 74 % yield. MS m/e 284 (M+NH4)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customchromatographed (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c80cfb0bb8ec48d098d5413a923f3aab
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

Loading…