Stannane, tributyl(1-ethoxyethenyl)- → HCID 21220947, compound

HRID 1584774Notes

Reaction equation

HRID 1584774 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH2:13]([O:15]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:14]>C1(C)C=CC=CC=1.[Pd].CCOCC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:13]([C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)(=[O:15])[CH3:14]

Participants

7

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 212208405-Bromo-1-benzofuran-7-carbaldehyde

Product 1

HCID 21220947HCID 21220947, compoundYield 72.4%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-bromo-benzofuran-7-carbaldehyde (2.00 g), 1-ethoxy-1-tributylstannanylethene (3.53 g)and bis(triphenylphosphine)palladium (II) chloride (63 mg) in dry toluene (4 ml) was heated at reflux under nitrogen for 18 h. A further portion of palladium catalyst (63 mg) was added and heating at reflux continued for a further 6 h. The reaction was allowed to cool, diluted with ether (40 ml) and filtered through a plug of Hyflo. The filtrate was washed successively with hydrochloric acid (50 ml; 2M) and brine (50 ml), then dried, and concentrated in vacuo to give an orange oil. Purification by FCC eluted with hexane to hexane:ethyl acetate (4:1) gave the title compound as a yellow powder (1.21 g), m.p. 91-93°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 18 h
  3. temperatureheating
  4. temperatureat reflux
  5. temperatureto cool
  6. filtrationfiltered through a plug of Hyflo
  7. washThe filtrate was washed successively with hydrochloric acid (50 ml; 2M) and brine (50 ml)
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customto give an orange oil
  11. customPurification by FCC
  12. washeluted with hexane to hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-bd967a1324bd4830aa584a2ff7576ec5
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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