Ammonium Chloride → HCID 58002934、化合物

HRID 1516713ノート

反応式

HRID 1516713 の反応式
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

参加物

10

反応物 4

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 58002968HCID 58002968、化合物HCID 178461828HCID 178461828、化合物

生成物 1

HCID 58002934HCID 58002934、化合物

試薬・触媒・溶媒 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9c4f06bbad0545d58fd82c7073356649
出典データセット
uspto-grants-2012_07
特許番号
US08227511B2

反応ノート

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