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

HRID 2173110Notes

Reaction equation

HRID 2173110 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].[Cl-].[Li+]>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>[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

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 6031445-Bromophthalide

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-2-benzofuran-1(3H)-one (6.68 g, 31.4 mmol) was combined with allyltributylstannane (12.5 g, 37.6 mmol), Pd(PPh3)4 (1.09 g, 0.941 mmol), and lithium chloride (2.66 g, 62.7 mmol) in toluene (100 mL) and the mixture was purged with nitrogen gas. The reaction mixture was then stirred at 100° C. for 4 h. The mixture was cooled to room temperature, filtered, and concentrated. The crude residue was purified by MPLC eluting in stepwise fashion with hexanes, then 10% ethyl acetate/hexanes, then 20% ethyl acetate/hexanes. 1H-NMR (500 MHz, CDCl3): δ ppm 7.87 (d, J=8 Hz, 1H), 7.39 (d, J=8 Hz, 1H), 7.35 (s, 1H), 5.96-6.04 (m, 1H), 5.32 (s, 2H), 5.15-5.20 (m, 2H), 3.55 (d, J=6.5 Hz, 2H).

Workup

  1. customthe mixture was purged with nitrogen gas
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by MPLC
  6. washeluting in stepwise fashion with hexanes

Sources & evidence

ORD record
ord-36d9253cd66b44e2ac94fa37844e5101
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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