Allyltributylstannane → 5-allyl-2-benzofuran-1(3H)-one

HRID 1848415Notes

Reaction equation

HRID 1848415 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14].[Li+].[Cl-]>C1(C)C=CC=CC=1.CCOC(C)=O.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>[CH2:14]([C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1)[CH:13]=[CH2:12]

Participants

7

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 6031445-Bromophthalide

Product 1

HCID 666439845-allyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5-bromo-2-benzofuran-1(3H)-one (15.0 g, 70.4 mmol), allyl-tributyl-stannane (25.6 g, 77.5 mmol), LiCl (11.8 g, 282 mmol) and Pd(PPh3)4 (1.2 g, 1.0 mmol) in 100 mL toluene was heated under N2 at 90-100° C. overnight. After cooling to r.t., the mixture was diluted with 250 mL EtOAc and filtered. The filtrate was washed with water and brine, dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified via column (DCM/Petrol Ether=1:5) to give the title compound.

Workup

  1. temperatureAfter cooling to r.t.
  2. filtrationfiltered
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified via column (DCM/Petrol Ether=1:5)

Sources & evidence

ORD record
ord-85ac98a5f6ed44f2870911b43060a881
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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