Methanesulfonyl chloride → 3-(3,4-Dimethoxyphenyl)propan-1-ol mesylate

HRID 908895Notes

Reaction equation

HRID 908895 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(N(CC)CC)C.ClCCl>[S:16]([O:14][CH2:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:18])(=[O:17])[CH3:15]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 775283-(3',4'-Dimethoxyphenyl)-1-propanol

Product 1

HCID 146225803-(3,4-Dimethoxyphenyl)propan-1-ol mesylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(3,4-dimethoxyphenyl)propan-1-ol (2.35 g) in triethylamine (2.5 mL) and dichloromethane (50 mL) stirred at a temperature close to 0° C. is added dropwise methanesulfonyl chloride (1.7 mL). The mixture is stirred overnight, concentrated under reduced pressure, dissolved in ethyl acetate. The organic layer is washed successively with water, a 0.1N aqueous hydrochloric solution, a saturated aqueous sodium hydrogenocarbonate solution and water, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with heptane/ethyl acetate 7/3 as eluent. Fractions containing the expected product are pooled and concentrated under reduced pressure to give 3 g of 3-(3,4-dimethoxyphenyl)propan-1-ol mesylate used without further purification.

Workup

  1. customclose to 0° C.
  2. concentrationconcentrated under reduced pressure
  3. dissolutiondissolved in ethyl acetate
  4. washThe organic layer is washed successively with water
  5. dry with materiala 0.1N aqueous hydrochloric solution, a saturated aqueous sodium hydrogenocarbonate solution and water, dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by chromatography over silica gel with heptane/ethyl acetate 7/3 as eluent
  8. additionFractions containing the expected product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-254fe281be984cb39874fe8ca30c371c
Source dataset
uspto-grants-2011_09
Patent number
US08017646B2

Reaction notes

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