Ammonium Chloride → HCID 86731311, compound

HRID 2277238Notes

Reaction equation

HRID 2277238 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([O:17][CH2:18][O:19][CH3:20])=[CH:12][N:11]=1)(C(C)(C)C)(C)C.[Cl-].[NH4+]>C1COCC1>[F:16][C:14]1[C:13]([O:17][CH2:18][O:19][CH3:20])=[CH:12][N:11]=[C:10]([CH2:9][OH:8])[CH:15]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 86731310HCID 86731310, compound

Product 1

HCID 86731311HCID 86731311, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-4-fluoro-5-(methoxymethoxy)pyridine (8.04 g) in THF (60 mL) was added 1 M tetrabutylammonium fluoride THF solution (34.7 mL), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate/methanol) to give the title compound (3.59 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-f7943cb8114445d59e26740d3172033a
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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