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

HRID 1474205Notes

Reaction equation

HRID 1474205 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

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 5-prop-2-en-1-yl-2-benzofuran-1(3H)-one.

Workup

  1. temperaturewas heated under N2 at 90˜100° C. overnight
  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-4c6b094a4daf4269a73b8b6ae5cad2a2
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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