Triethylamine → HCID 11051825, compound

HRID 1760208Notes

Reaction equation

HRID 1760208 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([OH:10])[C:7]#[C:8][CH3:9].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:10][CH2:6][C:7]#[C:8][CH3:9])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 129912-Butyn-1-olHCID 31297Methanesulfonyl chloride

Product 1

HCID 11051825HCID 11051825, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

305 ml methanesulfonyl chloride was added dropwise to a solution of 138 g 2-butyn-1-ol and 683 ml triethylamine in 2.7 L methylene chloride under ice-cooling, and the mixture was stirred at 0° C. for 1 hour and 40 minutes. Ice was added to the reaction solution under ice-cooling, and this mixture was extracted with methylene chloride. The organic layer was successively washed with 1M aqueous hydrochloric acid, a saturated aqueous sodium bicarbonate solution and brine, and the organic layer was dried over magnesium sulfate. This organic layer was filtered and then the solvent was evaporated, to give a dark brown oil (280 g, 96%).

Workup

  1. temperaturecooling
  2. additionIce was added to the reaction solution under ice-
  3. temperaturecooling
  4. extractionthis mixture was extracted with methylene chloride
  5. washThe organic layer was successively washed with 1M aqueous hydrochloric acid
  6. dry with materiala saturated aqueous sodium bicarbonate solution and brine, and the organic layer was dried over magnesium sulfate
  7. filtrationThis organic layer was filtered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-05ec5e9c766a4a9f9032375d112ebb51
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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