Pyridine → Methyl 9-[(methanesulfonyl)oxy]nonanoate

HRID 2222722Notes

Reaction equation

HRID 2222722 reaction equation
ClCCl.[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O>[CH3:23][S:24]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 292983Nonanoic acid, 9-hydroxy-, methyl ester

Product 1

HCID 22939818Methyl 9-[(methanesulfonyl)oxy]nonanoateYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Dichloromethane (20 mL) was added with methyl 9-hydroxynonanoate (2.1 g) and pyridine (1.8 g), stirred at 0° C., added with methanesulfonyl chloride (1.3 mL), gradually warmed to room temperature and stirred for one day. The reaction solution was added with water and then extracted twice with dichloromethane. The resulting organic layer was washed with 1 N hydrochloric acid and saturated sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was removed. The resulting residue was purified by silica gel column chromatography to obtain methyl 9-(methanesulfonyloxy)nonanoate (2.1 g, yield: 68%).

Workup

  1. temperaturegradually warmed to room temperature
  2. stirringstirred for one day
  3. extractionextracted twice with dichloromethane
  4. washThe resulting organic layer was washed with 1 N hydrochloric acid and saturated sodium hydrogencarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-625b82f5b50f49aea9f67ae4431dfee5
Source dataset
uspto-grants-2008_05
Patent number
US07371877B2

Reaction notes

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