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

HRID 1848404Notes

Reaction equation

HRID 1848404 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].[Cl-].[Li+]>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.C1(C)C=CC=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

To a flask charged with 5-bromo-4-methyl-2-benzofuran-1(3H)-one (320 mg, 1.409 mmol) and a stir bar was added allyl tri-n-butyltin (0.655 mL, 2.11 mmol), Pd(PPh3)4 (244 mg, 0.211 mmol), lithium chloride (179 mg, 4.23 mmol), and toluene (15 mL). The reaction was purged with nitrogen 2 times then was heated at reflux for 4 hours. The product was separated by silica gel chromatography to give 4-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one.

Workup

  1. customThe reaction was purged with nitrogen 2 times
  2. temperaturethen was heated
  3. temperatureat reflux for 4 hours
  4. customThe product was separated by silica gel chromatography

Sources & evidence

ORD record
ord-bdca25ca03cf434594a989bf573bdb3a
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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