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

HRID 1363876Notes

Reaction equation

HRID 1363876 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].N1C=CC=CC=1.ClCCl.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O>[CH3:23][S:24]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[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]nonanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 9-hydroxynonanoate and pyridine were added to dichloromethane. The solution was stirred at 0° C., added with methanesulfonyl chloride, and further stirred with gradually warming up to room temperature. The solution was added with water, and extracted twice with dichloromethane. The resulting organic layer was washed with 1N hydrochloric acid and saturated sodium hydrogen carbonate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed and the residue was purified by silica gel column chromatography to obtain methyl 9-(methanesulfonyloxy)nonanoate.

Workup

  1. stirringfurther stirred
  2. temperaturewith gradually warming up to room temperature
  3. extractionextracted twice with dichloromethane
  4. washThe resulting organic layer was washed with 1N hydrochloric acid and saturated sodium hydrogen carbonate
  5. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1250e83c3168489b8043280265ae1f02
Source dataset
uspto-grants-2011_02
Patent number
US07887835B2

Reaction notes

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