Isopropylethanediol → 2-Isopropoxyethyl Methanesulfonate

HRID 2041335Notes

Reaction equation

HRID 2041335 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][OH:7])([CH3:3])[CH3:2].[CH3:8][S:9](Cl)(=[O:11])=[O:10].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]([O:4][CH2:5][CH2:6][O:7][S:9]([CH3:8])(=[O:11])=[O:10])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7996IsopropylethanediolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 184650452-Isopropoxyethyl MethanesulfonateYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-isopropoxyethanol (2.0 mL, 17.37 mmol) in DCM (100 mL) at ambient temperature add methanesulfonyl chloride (1.48 mL, 18.08 mmol). Add triethylamine (2.70 mL, 19.37 mmol) slowly followed by DMAP (catalytic). Continue stirring overnight and concentrate in vacuo. Add diethyl ether and filter. Wash the filtrate with aqueous 1N aqueous HCl, brine, and saturated aqueous NaHCO3. Dry over anhydrous MgSO4 and concentrate in vacuo to give the desired intermediate (2.97 g, 94%).

Workup

  1. concentrationconcentrate in vacuo
  2. filtrationAdd diethyl ether and filter
  3. washWash the filtrate with aqueous 1N aqueous HCl, brine, and saturated aqueous NaHCO3
  4. dry with materialDry over anhydrous MgSO4
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f9cb6a5ae4194ea58effde04ce90768e
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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