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

HRID 1502034Notes

Reaction equation

HRID 1502034 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 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 silica column chromatography (DCM/Petrol Ether=1:5) to give 5-(prop-2-en-1-yl)-2-benzofuran-1(3H)-one.

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 silica column chromatography (DCM/Petrol Ether=1:5)

Sources & evidence

ORD record
ord-dbecd6daa76d463a9b6b031483850d64
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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