Iodine → HCID 86712326, 화합물

HRID 592449

반응식

HRID 592449 반응식
[C:1]1([C:7]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.C(O[I:20](C1C=CC=CC=1)OC(=O)C)(=O)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[I:20][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:7]1([C:11]([OH:13])=[O:12])[CH2:8][CH2:9][CH2:10]1

참가 물질

6

반응물 3

HCID 807Iodine3회HCID 76724Iodobenzene diacetate3회HCID 2771711-Phenylcyclobutanecarboxylic acid

생성물 1

HCID 86712326HCID 86712326, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A solution of 1-phenyl-1-cyclobutanecarboxylic acid (2.00 g, 11.4 mmol) in DMF (10 mL) containing palladium (II) acetate (0.109 g, 0.567 mmol), iodine (2.16 g, 8.51 mmol) and (diacetoxyiodo)benzene (2.47 g, 8.51 mmol) was stirred at 60° C. for 18 hours in the absence of light. Additional iodine (2.16 g, 8.51 mmol) and (diacetoxyiodo)benzene (2.47 g, 8.51 mmol) were added and stirring was continued at 60° C. for 8 hours. A final addition of iodine (2.16 g, 8.51 mmol) and (diacetoxyiodo)benzene (2.47 g, 8.51 mmol) was performed and stirring was continued at 60° C. for 16 hours. The reaction mixture was partitioned between EtOAc and water and the aqueous phase was extracted several times with EtOAc. The combined organic fractions were washed with 10% sodium metabisulfate (3×30 mL), 10% citric acid (2×30 mL), water, brine, and then dried (MgSO4), filtered and the solvent evaporated. The crude product was dry loaded onto silica gel and the product was separated using silica column chromatography (Biotage Isolera, 40 g SiO2 Cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A52 as a cream solid (425 mg, 12%). LCMS-A: rt 5.711 min.

후처리

  1. stirringstirring
  2. waitwas continued at 60° C. for 8 hours
  3. stirringstirring
  4. waitwas continued at 60° C. for 16 hours
  5. customThe reaction mixture was partitioned between EtOAc and water
  6. extractionthe aqueous phase was extracted several times with EtOAc
  7. washThe combined organic fractions were washed with 10% sodium metabisulfate (3×30 mL), 10% citric acid (2×30 mL), water, brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent evaporated
  11. dry with materialThe crude product was dry
  12. customthe product was separated
  13. customsilica column chromatography (Biotage Isolera, 40 g SiO2 Cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.)

출처 및 근거

ORD 기록
ord-5c5d78fd6b2745cb92442f6b61dc5d26
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238644B2

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