Hydrofluoric Acid → HCID 21830705, compound

HRID 1600927Notes

Reaction equation

HRID 1600927 reaction equation
F.[F:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]([O:26][Si](C(C)(C)C)(C)C)[CH2:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[F:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH:17]([OH:26])[CH2:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 21830644HCID 21830644, compound

Product 1

HCID 21830705HCID 21830705, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Hydrofluoric acid (40%, 4 ml) was added to a solution of (±)-3-(4-(3'-fluorobiphenyl-4-yloxy)-3-(tert-butyldimethylsilyloxy)butyl)pyridine in acetonitrile (30 ml) and the mixture stirred for 2 days. The solution was neutralised by careful addition to a saturated aqueous solution of sodium bicarbonate (200 ml). The mixture was extracted with ethyl acetate, the organic extract dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified twice by column chromatography over silica eluting with dichloromethane then ethyl acetate to give the title compound as a white powder (0.33 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionthe organic extract
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified twice by column chromatography over silica eluting with dichloromethane

Sources & evidence

ORD record
ord-2dd34b6e665841238cdcbc03ec65c973
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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