Isopropylethanediol → 2-Isopropoxyethyl Methanesulfonate

HRID 911455Notes

Reaction equation

HRID 911455 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-9db026b4937c4f068305c4dc4018dca8
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…