Triethylamine → 3-Methoxyphenethyl mesylate

HRID 568779Notes

Reaction equation

HRID 568779 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 787243-Methoxyphenethyl alcohol

Product 1

HCID 130615423-Methoxyphenethyl mesylateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a flask under argon was added 10.1 g (0.0661 mole) 3-methoxyphenethyl alcohol, 150 mL methylene chloride and 9.2 ml (0.0661 mole) triethylamine. The solution was cooled to 0° C. and 5.1 ml (0.0661 mole) methanesulfonyl chloride was added slowly. The reaction mixture was warmed to room temperature. After 24 hr, the reaction was washed with water and brine, and dried with MgSO4. The solvent was evaporated in vacuo to give 15.0 g of the product as a clear oil.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. washthe reaction was washed with water and brine
  3. dry with materialdried with MgSO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6c28129db84e4fc69e5d5e66e6fd20c1
Source dataset
uspto-grants-1988_03
Patent number
US04729994

Reaction notes

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