Triethylamine → Hex-5-yn-1-yl methanesulfonate

HRID 1197313Notes

Reaction equation

HRID 1197313 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([OH:12])[CH2:7][CH2:8][CH2:9][C:10]#[CH:11].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:12][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 702345-Hexyn-1-ol

Product 1

HCID 12714590Hex-5-yn-1-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphonyl chloride (23.7 ml) in dry dichloromethane (25 ml.) was added dropwise to a solution of hex-5-yn-1-ol (Lancaster Synthesis, 25 g) and triethylamine (47.3 ml) in dichloromethane (300 ml), stirred under a nitrogen atmosphere at -70°. The resulting mixture was allowed to warm to room temperature over 16 hours. The mixture was then washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. Hex-5-ynyl methanesulphonate was obtained as an oil (43.6 g) and was used without purification.

Workup

  1. washThe mixture was then washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
  2. dry with materialbefore drying over anhydrous magnesium sulphate and evaporation in vacuo

Sources & evidence

ORD record
ord-d188efe2fb264940b21559ab9d50ed11
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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