Sodium Hydroxide → 6-[(Methylsulfonyl)methyl]pyridin-3-ol

HRID 1042115Notes

Reaction equation

HRID 1042115 reaction equation
C1(S([O:10][C:11]2[CH:12]=[N:13][C:14]([CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:15][CH:16]=2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:21][S:18]([CH2:17][C:14]1[N:13]=[CH:12][C:11]([OH:10])=[CH:16][CH:15]=1)(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86661828HCID 86661828, compound

Product 1

HCID 667261886-[(Methylsulfonyl)methyl]pyridin-3-olYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-[(methylsulfonyl)methyl]pyridin-3-yl benzenesulfonate (30 g) in ethanol (200 mL) and tetrahydrofuran (200 mL) was added 1N aqueous sodium hydroxide solution (190 mL), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was concentrated, 1N hydrochloric acid (190 mL) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (13.9 g, yield 79%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N hydrochloric acid (190 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb5bce4dccd94a24a7e3cc6d3424c38c
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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