Tetrahydrofuran → HCID 58201187, compound

HRID 882986Notes

Reaction equation

HRID 882986 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Si]([O:31][CH2:32][C:33]1[C:38]([CH3:39])=[C:37]([O:40][CH3:41])[C:36]([F:42])=[CH:35][N:34]=1)(C(C)(C)C)(C)C>ClCCl>[F:42][C:36]1[C:37]([O:40][CH3:41])=[C:38]([CH3:39])[C:33]([CH2:32][OH:31])=[N:34][CH:35]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 58201208HCID 58201208, compound

Product 1

HCID 58201187HCID 58201187, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetrabutylammonium fluoride (1 M solution, 1.49 ml) was added to a tetrahydrofuran (10 ml) solution of the above 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-fluoro-4-methoxy-3-methylpyridine (353 mg) under cooling in an ice bath, and the resulting mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with dichloromethane, and was then washed with water. The organic layer was dried over anhydrous sodium sulfate, and the filtrate was then concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain the title compound (150 mg) as a solid.

Workup

  1. temperatureunder cooling in an ice bath
  2. washwas then washed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationthe filtrate was then concentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7b0ae9d3c8b041c4b8cdab2144da791d
Source dataset
uspto-grants-2012_08
Patent number
US08236813B2

Reaction notes

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