Triethylamine → 2-Mesyloxyethyl-1,4-benzodioxan

HRID 1420369Notes

Reaction equation

HRID 1420369 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-b493e07b2893439ab9bd99aabdcb2fca
Source dataset
uspto-grants-1999_03
Patent number
US05889035

Reaction notes

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