Pyridine → 4-(Methoxymethoxy)cyclohexane 1,1-dimethyl dimethanesulfonate

HRID 1059300Notes

Reaction equation

HRID 1059300 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][C:8]([CH2:13][OH:14])(CO)[CH2:7][CH2:6]1.N1C=CC=CC=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:21][S:22]([O:14][CH3:13])(=[O:24])=[O:23].[CH3:21][S:22]([O:14][CH3:13])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 186703154-(Methoxymethoxy)-1,1-cyclohexanedimethanol

Product 1

HCID 865922754-(Methoxymethoxy)cyclohexane 1,1-dimethyl dimethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.84 g of 4-(methoxymethoxy)cyclohexane-1,1-dimethanol was dissolved in 110 ml of dichloromethane and 13.56 g of pyridine was added thereto and ice-cooled. 7.79 ml of methanesulfonyl chloride was added thereto and the resulting mixture was stirred at room temperature for 17 hours. Then the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 11.91 g of the title compound as a colorless oily substance.

Workup

  1. temperatureice-cooled
  2. concentrationThen the reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-10eaa4b7055e4991a057692b43b4c652
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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