Triethylamine → 2-Mesyloxyethyl-1,4-benzodioxan

HRID 976710Notes

Reaction equation

HRID 976710 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.C(N(CC)CC)C.[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>ClCCl>[S:21]([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)([CH3:24])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 98334Ethanol, 2-(1,4-benzodioxan-2-yl)-

Product 1

HCID 153801072-Mesyloxyethyl-1,4-benzodioxan

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the compound 2-hydroxyethyl-1,4-benzodioxan (11.96 g) in dichloromethane (450 ml) was added triethylamine (0.12 mol, 10 ml). Mesylchloride (9.2 g) was then added dropwise and the reaction mixture was stirred for one hour at room temperature. After completion of 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 of 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-261422b7ed704cb59643a98940779ff5
Source dataset
uspto-grants-1997_03
Patent number
US05612342

Reaction notes

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