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

HRID 2037492Notes

Reaction equation

HRID 2037492 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].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)Cl>[CH:1]([C:4]1([CH2:9][CH2:10][O:11][S:13]([CH3:12])(=[O:15])=[O:14])[O:8][CH2:7][CH2:6][O:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 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 115.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethanol (11 g, 0.069 mol) and TEA (20.91 g, 0.207 mol) in dried CH2Cl2 (110 mL) was added MsCl (15.8 g, 0.138 mol) dropwise at 0° C. The mixture was stirred till the reaction was over. The reaction was quenched with water. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic phase was dried over Na2SO4, and concentrated to give the crude methanesulfonic acid 2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl ester (19 g, crude), which was used for the next step without further purification.

Workup

  1. customThe reaction was quenched with water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0942d0e5a67d42a2b65780016e204794
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…