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Tributylvinyltin → HCID 21476907, 화합물

HRID 2293580
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HRID 2293580 반응식
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1OS(C(F)(F)F)(=O)=O)[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH3:3].[CH:22]([Sn](CCCC)(CCCC)CCCC)=[CH2:23]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH:22]=[CH2:23])[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH3:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 81998TributylvinyltinHCID 21476928HCID 21476928, 화합물

생성물 1

HCID 21476907HCID 21476907, 화합물수율 63%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of 8.053 g (24.7 mmol) of the product of Step A and 8.136 g (25.7 mmol) of vinyltributyltin in 50 mL of anhydrous DMF was added 0.520 g (0.74 mmol) of bis(triphenylphosphine)palladium(II) chloride, the mixture was freed of air by alternate vacuum and nitrogen flush cycles, and the reaction mixture was magnetically stirred at 60° C. for 6 hours. The reaction mixture was then cooled to room temperature, partitioned between EtOAc and saturated brine, and extracted. The organic layer was washed three times with brine, separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 3% EtOAc in hexane. Evaporation of the purified fractions and drying in vacuo afforded 3.176 g (63%) of the title compound as a clear oil.

후처리

  1. customflush cycles
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. custompartitioned between EtOAc and saturated brine
  4. extractionextracted
  5. washThe organic layer was washed three times with brine
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 3% EtOAc in hexane
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

출처 및 근거

ORD 기록
ord-092bea7a989445a7aeb0425cee1eb2b2
출처 데이터셋
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05686478

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