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

HRID 914645Notes

Reaction equation

HRID 914645 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-0244de36b0c44eb59446bbf75a78a0e3
Source dataset
uspto-grants-2007_09
Patent number
US07264790B2

Reaction notes

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