Ammonium Chloride → HCID 58002934, 화합물

HRID 1516713노트

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HRID 1516713 반응식
FC(F)(F)S(O[C:7]1[CH:19]=[C:18]2[C:10]([C:11](=[O:20])[CH2:12][C:13]3([O:17]2)[CH2:16][CH2:15][CH2:14]3)=[C:9]([OH:21])[CH:8]=1)(=O)=O.[Cl-].[Li+].[CH:26]([Zn]C(C)C)([CH3:28])[CH3:27].[Cl-].[NH4+]>O.Cl.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C)C=O>[OH:21][C:9]1[CH:8]=[C:7]([CH:26]([CH3:28])[CH3:27])[CH:19]=[C:18]2[C:10]=1[C:11](=[O:20])[CH2:12][C:13]1([O:17]2)[CH2:16][CH2:15][CH2:14]1

참가 물질

10

반응물 4

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 58002968HCID 58002968, 화합물HCID 178461828HCID 178461828, 화합물

생성물 1

HCID 58002934HCID 58002934, 화합물

시약·촉매·용매 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Under argon, 16 g (45.42 mmol) of 5-hydroxy-4-oxo-3,4-dihydrospiro[chromen-2,1′-cyclobutan]-7-yl trifluoromethanesulfonate (Example 44A), 3.71 g (4.54 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and 5.78 g (136.25 mmol) of lithium chloride are suspended in 400 ml of abs. dimethylformamide. The mixture is cooled to 0° C., 90.8 ml (90.8 mmol) of diisopropylzinc (1 M solution in toluene) are added and the mixture is stirred at this temperature for 4 hours. At 0° C., saturated ammonium chloride solution is then added to the mixture. The mixture is diluted with water, 1 N hydrochloric acid and ethyl acetate, the organic phase is separated off and the aqueous phase is extracted repeatedly with ethyl acetate. The combined organic phases are washed twice with water and once with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is adsorbed on silica gel and purified on a silica gel column (mobile phase: cyclohexane→cyclohexane/ethyl acetate 20:1). This gives 9.6 g (86% of theory) of the title compound.

후처리

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted repeatedly with ethyl acetate
  3. washThe combined organic phases are washed twice with water and once with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a silica gel column (mobile phase: cyclohexane→cyclohexane/ethyl acetate 20:1)

출처 및 근거

ORD 기록
ord-9c4f06bbad0545d58fd82c7073356649
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227511B2

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