Water → HCID 90203660, compound

HRID 927046Notes

Reaction equation

HRID 927046 reaction equation
[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][O:18]C(=O)C)=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.[OH-].[Na+]>C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][OH:18])=[N:15][CH:16]=2)=[CH:22][CH:23]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 90203439HCID 90203439, compound

Product 1

HCID 90203660HCID 90203660, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetic acid 5-(4-methanesulfonyl-benzyloxy)-pyridin-2-ylmethyl ester (10.4 g, 31 mmol) was suspended in a water (20 mL) and ethanol (80 mL). To this was added NaOH (2.2 g, 55 mmol) and the reaction was heated to reflux for 2 h. The reaction mixture was cooled to rt and stirred for 24 h and then concentrated under reduced pressure. The resulting residue was partitioned between water and ethyl acetate. The organic layer was dried over Na2SO4, filtered and volatiles were removed under reduced pressure to yield [5-(4-methanesulfonyl-benzyloxy)-pyridin-2-yl]-methanol (4.04 g, 44%) as a light yellow solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was partitioned between water and ethyl acetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customvolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-d55b9149f42041baab3f14dcc34e5755
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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