Dimethylformamide → HCID 53783583, compound

HRID 1600952Notes

Reaction equation

HRID 1600952 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[H-].[Na+].F.[OH-:20].[Na+].[CH3:22][N:23]([CH3:26])C=O>C(#N)C.O>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:6][C@H:7]([OH:20])[CH2:8][CH2:9][C:4]3[CH:26]=[N:23][CH:22]=[CH:2][CH:1]=3)=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 14917Hydrofluoric AcidHCID 24758Sodium hydrideHCID 112181061-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone

Product 1

HCID 53783583HCID 53783583, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Prepared according to method described in Example 26e) from 3'-acetylbiphenyl-4-ol (Example 55b), 0.59 g), (2R)-4-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-(4-toluenesulfonyloxy)butane (1.0 g) and sodium hydride (60% dispersion in mineral oil, 0.12 g) in dry N,N-dimethylformamide (10 ml). Crude material from this reaction was dissolved in acetonitrile (15 ml) and treated with hydrofluoric acid (40%, 5 ml). The reaction mixture was stirred at room temperature for 18 hours and then poured into water (25 ml). The pH was adjusted to 9 by adding sodium hydroxide solution (2 M). The mixture was then extracted with ethyl acetate (3×100 ml) and the combined extracts dried over anhydrous magnesium sulfate. The solution was filtered and then concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate to give the title compound as a white solid (0.25 g).

Workup

  1. customPrepared
  2. extractionThe mixture was then extracted with ethyl acetate (3×100 ml)
  3. dry with materialthe combined extracts dried over anhydrous magnesium sulfate
  4. filtrationThe solution was filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-184c5c9528b34d6a8fd95ef4792b7da6
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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