Triethylamine → 2-(2-Isopropyl-1,3-dioxolan-2-yl)ethyl methanesulfonate

HRID 80980

Reaction equation

HRID 80980 reaction equation
[CH:1]([C:4]1([CH2:9][CH2:10][OH:11])[O:8][CH2:7][CH2:6][O:5]1)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH:1]([C:4]1([CH2:9][CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])[O:8][CH2:7][CH2:6][O:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 141623372-[2-(Propan-2-yl)-1,3-dioxolan-2-yl]ethan-1-ol

Product 1

HCID 107051032-(2-Isopropyl-1,3-dioxolan-2-yl)ethyl methanesulfonateYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-isopropyl-1,3-dioxolan-2-yl)-ethanol (8.0 g, 50 mmol) and triethylamine (23.5 mL, 170 mmol) in anhydrous CH2Cl2 (120 mL) was added methanesulfonyl chloride (11.6 mL, 150 mmol) at 0° C., and the reaction mixture was stirred at room temperature till the reaction was finished. The reaction mixture was washed with water and brine, dried over Na2SO4, filtered, and concentrated to give the crude methanesulfonic acid 2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl ester (12 g), which was used for the next step without further purification.

Workup

  1. washThe reaction mixture was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1a15484b2a5546a3a8afc2433a8478aa
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Linked notes

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