Allyltributylstannane → HCID 57682917, compound

HRID 494929Notes

Reaction equation

HRID 494929 reaction equation
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[O:8][C:4]=2[CH:3]=1.[CH2:14]([Sn](CCCC)(CCCC)CCCC)[CH:15]=[CH2:16]>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>[CH2:16]([C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[O:8][C:4]=2[CH:3]=1)[CH:15]=[CH2:14]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 57682901HCID 57682901, compound

Product 1

HCID 57682917HCID 57682917, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

400 mg of 6-bromo-5-methoxy-2-methylbenzoxazole was dissolved in 5 ml of toluene. Thereafter, 769 μl of allyl tributyl tin and 57 mg of tetrakis(triphenylphosphine)palladium were successively added to the reaction solution. Thereafter, the reaction solution was heated to reflux under nitrogen atmosphere. Approximately 14 hours later, the reaction solution was stood to cool and then filtered through celite, followed by concentration under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 202 mg of the subject compound.

Workup

  1. temperatureThereafter, the reaction solution was heated
  2. temperatureto reflux under nitrogen atmosphere
  3. customApproximately 14 hours
  4. temperatureto cool
  5. filtrationfiltered through celite
  6. concentrationfollowed by concentration under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-efa549ae91f34055bafa00113f3bc28b
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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