N-Fluorobenzenesulfonimide → HCID 86731310, compound

HRID 2277237Notes

Reaction equation

HRID 2277237 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[CH:12][N:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCCCCC.C([Li])CCC.[F:31]N(S(C1C=CC=CC=1)(=O)=O)S(C1C=CC=CC=1)(=O)=O>C1COCC1.[Cl-].[Na+].O>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([F:31])[C:13]([O:16][CH2:17][O:18][CH3:19])=[CH:12][N:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 86731309HCID 86731309, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 86731310HCID 86731310, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-(((tert-butyl(dimethyl)silyl)oxy)methyl)-5-(methoxymethoxy)pyridine (13.5 g) in THF (100 mL) was added 1.6 M n-butyllithium hexane solution (38.6 mL) at −78° C., and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (19.5 g) at −78° C., and the mixture was allowed to warm to room temperature, and stirred for 30 min. To the reaction mixture was added saturated brine, 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) to give the title compound (7.49 g).

Workup

  1. stirringstirred for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-344aef860e104685a88a4113904c0d6d
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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