Water → HCID 19377393, compound

HRID 2210747Notes

Reaction equation

HRID 2210747 reaction equation
[F:1][CH2:2][CH:3]([C:5]1[C:6]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4].[C:19](OC(=O)C)(=[O:21])[CH3:20].O.OS(O)(=O)=O>C1COCC1>[C:19]([O:4][CH:3]([C:5]1[C:6]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][CH:8]=[CH:9][CH:10]=1)[CH2:2][F:1])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 19377389HCID 19377389, compound

Product 1

HCID 19377393HCID 19377393, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(2-fluoro-1-hydroxyethyl)-2-(phenylmethylthio)pyridine (16 g) in dry THF and acetic anhydride (7.4 g) is stirred with a catality amount of4-dimethylaminopyridine at room temperature for 12 hours. The reaction mixture is then poured into water and neutralized with dilute H2SO4. The mixture is extracted three times with methylene chloride, the combined extracts are dried (MgSO4), evaporated to obtain the desired product (oil, 17.2 g, Yield: 93%).

Workup

  1. extractionThe mixture is extracted three times with methylene chloride
  2. dry with materialthe combined extracts are dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-71545e45aa8646cda2126ebaef1c1610
Source dataset
uspto-grants-1995_10
Patent number
US05461026

Reaction notes

Loading…