Triethylamine → 1-(9-Dodecynyl) methanesulfonate

HRID 2254532Notes

Reaction equation

HRID 2254532 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH2:18][CH3:19].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:20][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH2:18][CH3:19])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1170119-Dodecyn-1-ol

Product 1

HCID 570472591-(9-Dodecynyl) methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (4.3 ml) was added to a solution of 9-dodecyn-1-ol (5.1 g, 28 mmol) in 50 ml CH2Cl2, and the mixture was then added dropwise at 0° C. to a solution of methanesulfonyl chloride (2,2 ml, 28 mmol) in 10 ml CH2Cl2. The mixture was stirred another 4 hours at room temperature, then cooled to 0°-5° C. The solution was washed with cold 5% aqueous sodium bicarbonate, cold 1N HCl, cold water, then saturated brine. The extract was dried over Na2SO4 and filtered and evaporated. The solvent was evaporated to leave crude 1-(9-dodecynyl) methanesulfonate.

Workup

  1. temperaturecooled to 0°-5° C
  2. washThe solution was washed with cold 5% aqueous sodium bicarbonate, cold 1N HCl, cold water
  3. dry with materialThe extract was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f8f1c0b6b7334178ac9b6aa7b0e42077
Source dataset
uspto-grants-1993_08
Patent number
US05236900

Reaction notes

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