Chloride → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl methanesulfonate
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].[Cl-]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21]Participants
6
Procedure
A solution of non-polydispersed triethylene glycol monomethyl ether molecules (4.00 mL, 4.19 g, 25.5 mmol) and triethylamine (4.26 mL, 3.09 g, 30.6 mmol) in dry dichloromethane (50 mL) was chilled in an ice bath and place under a nitrogen atmosphere. A solution of methanesulfonyl chloride (2.37 mL, 3.51 g, 30.6 mmol) in dry dichloromethane (20 mL) was added dropwise from an addition funnel. Ten minutes after the completion of the chloride addition, the reaction mixture was removed from the ice bath and allowed to come to room temperature. The mixture was stirred for an additional hour, at which time TLC (CHCl3 with 15% MeOH as the elutant) showed no remaining triethylene glycol monomethyl ether.
Workup
- customthe reaction mixture was removed from the ice bath
- customto come to room temperature
Sources & evidence
- ORD record
- ord-c681443fbe9c465ebaaf598f9830ab68
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06835802B2
Reaction notes
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