Tetrahydrofuran → HCID 117839522, compound

HRID 1477617Notes

Reaction equation

HRID 1477617 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:12][C:13]([F:30])([F:29])[S:14]([O:17][C:18]1[CH:28]=[CH:27][C:21]([C:22](OCC)=[O:23])=[CH:20][N:19]=1)(=[O:16])=[O:15].[OH-].[Na+]>C(OCC)(=O)C>[F:30][C:13]([F:12])([F:29])[S:14]([O:17][C:18]1[CH:28]=[CH:27][C:21]([CH2:22][OH:23])=[CH:20][N:19]=1)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 102017352HCID 102017352, compound

Product 1

HCID 117839522HCID 117839522, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (2.0 mL) of lithium aluminum hydride (19.0 mg, 0.450 mmol), ethyl 6-{[(trifluoromethyl)sulfonyl]oxy}nicotinate (112 mg, 0.375 mmol) was added and the resultant solution was stirred at 0° C. for 5 minutes. After completion of the reaction, 1 M sodium hydroxide aqueous solution, Celite, and ethyl acetate were added to the reaction solution and the resultant mixture was filtered with Celite, followed by extraction from the filtrate with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product of the title compound (62.9 mg).

Workup

  1. additionwere added to the reaction solution
  2. filtrationthe resultant mixture was filtered with Celite
  3. extractionfollowed by extraction from the filtrate with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08c57f6e3bf7458b9b3f5af8ad42575d
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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