Methanesulfonyl chloride → 2-Mesyloxyethyl-1,4-benzodioxan

HRID 2184524Notes

Reaction equation

HRID 2184524 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH2:5]1.[S:14](Cl)([CH3:17])(=[O:16])=[O:15]>ClCCl.C(N(CC)CC)C>[S:14]([O:1][CH2:2][CH2:3][CH:4]1[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH2:5]1)([CH3:17])(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 98334Ethanol, 2-(1,4-benzodioxan-2-yl)-

Product 1

HCID 153801072-Mesyloxyethyl-1,4-benzodioxanYield 99.6%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

To the compound 2-hydroxyethyl-1,4-benzodioxan (11.96 g) in dichloromethane (450 ml) was added triethylamine (0.12 mmol, 10 ml). Mesylchloride (9.2 g) was then added dropwise and the reaction mixture was stirred for one hour at room temperature. After completion or the reaction, the solution was washed with water, brine, and concentrated to an oil, which was purified by chromatography on silica gel to yield 2-mesyloxyethyl-1,4-benzodioxan 17.08 g.

Workup

  1. customAfter completion or the reaction
  2. washthe solution was washed with water, brine
  3. concentrationconcentrated to an oil, which
  4. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-71e0051bbd854617b68674d70798aaa2
Source dataset
uspto-grants-2002_06
Patent number
USRE037729E1

Reaction notes

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