Stannane, tributyl(1-ethoxyethenyl)- → HCID 66646735, compound

HRID 1187047Notes

Reaction equation

HRID 1187047 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[C:4]([CH3:12])[C:3]=1[CH:13]1[CH2:15][O:14]1.C([Sn](CCCC)(CCCC)C(OCC)=C)CCC>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>[C:13]([C:3]1[C:4]([CH3:12])=[CH:5][C:6]2[C:7](=[O:11])[O:8][CH2:9][C:10]=2[C:2]=1[CH3:1])(=[O:14])[CH3:15]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 59568660HCID 59568660, compound

Product 1

HCID 66646735HCID 66646735, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a 20 mL microwave tube containing a stir bar were added 4,6-dimethyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one (from the synthesis of INTERMEDIATE 9, 1.0 g, 4.2 mmol), tetrakis(triphenylphosphine)palladium (0) (0.240 g, 0.207 mmol), and tributyl(1-ethoxy-vinyl)tin (2.20 g, 6.22 mmol); to the mixture was added anhydrous toluene (18 mL) and the tube was capped, degassed and purged with N2. The tube was then placed in an oil bath and heated at 110° C. for 12 h; LC indicated some product formation. The tube was taken out of the oil bath and cooled to room temperature. The solution was concentrated to dryness under reduced pressure and the resulting residue was then treated with 4M HCl (10 mL); the resulting solution was stirred at room temperature for 1 h; LC analysis indicated completion of the reaction. The solution was concentrated to dryness and the residue was re-dissolved in DCM, was absorbed in silica gel and was then loaded into silica column for separation with the solvent systems of Hexanes/EtOAc (1/1); this yielded 5-acetyl-4,6-dimethyl-2-benzofuran-1(3H)-one.

Workup

  1. additionTo a 20 mL microwave tube containing a stir bar
  2. customthe tube was capped
  3. customdegassed
  4. custompurged with N2
  5. customThe tube was then placed in an oil bath
  6. temperaturecooled to room temperature
  7. concentrationThe solution was concentrated to dryness under reduced pressure
  8. additionthe resulting residue was then treated with 4M HCl (10 mL)
  9. customcompletion of the reaction
  10. concentrationThe solution was concentrated to dryness
  11. dissolutionthe residue was re-dissolved in DCM
  12. customwas absorbed in silica gel
  13. customwas then loaded into silica column for separation with the solvent systems of Hexanes/EtOAc (1/1)

Sources & evidence

ORD record
ord-c2723c83e50e4026931932d052c5a28f
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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