Methanesulfonyl chloride → HCID 20306015, compound

HRID 1732338Notes

Reaction equation

HRID 1732338 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:9]=1[O:10][CH2:11][CH2:12][OH:13]>N1C=CC=CC=1>[S:2]([O:13][CH2:12][CH2:11][O:10][C:9]1[C:8]([O:7][CH3:6])=[CH:17][CH:16]=[CH:15][C:14]=1[O:18][CH3:19])(=[O:4])(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 142576012-(2,6-Dimethoxyphenoxy)ethan-1-ol

Product 1

HCID 20306015HCID 20306015, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (23 g.) was added dropwise to a stirred solution of 2-[2,6-dimethoxyphenoxy]ethanol (20 g.) (J. Med. Chem. 1969, 12, 326) in pyridine (50 ml.). The solution was left at room temperature for 60 hours, then the solvent evaporated under reduced pressure. The residue was taken up in chloroform, washed with water (3×100 ml.) and sodium bicarbonate solution (5%, 3×100 ml.), dried and the solvent evaporated. The residue was triturated with n-hexane and the solid collected to give 2-[2,6-dimethoxyphenoxy]-ethyl mesylate (11.3 g.) characterized spectroscopically.

Workup

  1. customthe solvent evaporated under reduced pressure
  2. washwashed with water (3×100 ml.) and sodium bicarbonate solution (5%, 3×100 ml.)
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was triturated with n-hexane
  6. customthe solid collected

Sources & evidence

ORD record
ord-0376ac52247c46a4a070b6e6b4f1e4ab
Source dataset
uspto-grants-1980_12
Patent number
US04237138

Reaction notes

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