Triethylamine → 2-Mesyloxyethyl-1,4-benzodioxan

HRID 2211513Notes

Reaction equation

HRID 2211513 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-0a12a7d1d9db47df90b9c4521eda85df
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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