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Potassium Hydroxide → (R)-3-(4-Hydroxy-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

HRID 1617966
ノート
印刷プレビュー

反応式

HRID 1617966 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[OH-:26].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[Cl-].[NH4+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[OH:26][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 66666695(R)-3-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

生成物 1

HCID 67015734(R)-3-(4-Hydroxy-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one収率 77%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a white suspension of (R)-3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (example 142, step 2, 200 mg) and potassium hydroxide (62.6 mg) in 1,4-dioxane (1 mL) and water (0.6 mL) under argon were added 2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-biphenyl (17.2 mg) and tris(dibenzylideneacetone)dipalladium(0) (9.3 mg). The reaction mixture was heated to 100° C. and stirred for 3 hours. A saturated aq. solution of ammonium chloride and ethyl acetate were added, the phases were separated and the inorganic one was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (30% to 100% ethyl acetate in heptane) to yield the title compound as a light yellow semisolid (77%), MS (ESI+): m/z=332.1 ([M+H]+).

後処理

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (30% to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-4866ceee68b84ff09b5b1188f2d4336e
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765730B2

反応ノート

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