Allyltributylstannane → 4-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one

HRID 2173170Notes

Reaction equation

HRID 2173170 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH3:12].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15].[Li+].[Cl-]>C1(C)C=CC=CC=1.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>[CH3:12][C:3]1[C:4]2[CH2:8][O:7][C:6](=[O:9])[C:5]=2[CH:10]=[CH:11][C:2]=1[CH2:15][CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 595687115-Bromo-4-methylisobenzofuran-1(3H)-one

Product 1

HCID 666465364-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5-bromo-4-methyl-2-benzofuran-1(3H)-one (980 mg, 4.3 mmol), allyl-tributyl-stannane (1.7 g, 5.2 mmol), LiCl (550 mg, 12.9 mmol) and Pd(PPh3)4 (0.1 g) in anhydrous toluene was stirred at reflux under N2 overnight. The solvent was removed under reduced pressure, and the residue was purified with silica gel column chromatography to give the product 4-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one.

Workup

  1. temperatureat reflux under N2 overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-f01f7474969a4258bb503e3c3db8decf
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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