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

HRID 1519645Notes

Reaction equation

HRID 1519645 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2.[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14].[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>[CH2:14]([C:2]1[CH:11]=[CH:10][C:9]2[C:7](=[O:8])[O:6][CH2:5][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

A 4-neck, 22-L, round bottom flask equipped with a mechanical stirrer, thermocouple, nitrogen bubbler, and condenser was charged with 5-bromophthalide (650 g, 3.0 mol), allyltri-n-butyltin (1200 g, 3.6 mol), tetrakis(triphenylphosphine)palladium (100 g, 0.089 mol), lithium chloride (250 g, 5.9 mol) and toluene (8.8 L). The mixture was evacuated and flushed with nitrogen 3 times and then was stirred at 100° C. for 4 hours. After slowly cooling to ambient temperature, the mixture was filtered and concentrated. The resulting solid was purified by silica gel column chromatography (heptane:ethyl acetate, 0→40%) to provide 5-allyl-2-benzofuran-1(3H)-one.

Workup

  1. customThe mixture was evacuated
  2. customflushed with nitrogen 3 times
  3. temperatureAfter slowly cooling to ambient temperature
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated
  6. customThe resulting solid was purified by silica gel column chromatography (heptane:ethyl acetate, 0→40%)

Sources & evidence

ORD record
ord-fa1ab5e388f945d7acef15a72fbcebb9
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…