Water → 2-Thienylmethyl methanesulfonate

HRID 1777353Notes

Reaction equation

HRID 1777353 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][OH:12].C(N(CC)CC)C.O>ClCCl>[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][O:12][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 694672-Thiophenemethanol

Product 1

HCID 189734302-Thienylmethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (6.2 mL, 0.0797 mol) is added dropwise to a solution of thiophene-2-methanol (7.0 g, 0.0613 mol) and triethyl amine (12.8 mL, 0.0920 mol) in dichloromethane (70 mL) at 0-5° C. The reaction mixture is allowed to stir at room temperature for 30 min. Demineralized water (25 mL) is added to the reaction mixture and the organic layer is separated. The aqueous layer is extracted with dichloromethane (1×25 mL). Combined organic layer is dried over anhydrous sodium sulfate. Removal of solvent under reduced pressure gives methanesulfonic acid thiophen-2-ylmethyl ester.

Workup

  1. customthe organic layer is separated
  2. extractionThe aqueous layer is extracted with dichloromethane (1×25 mL)
  3. dry with materialCombined organic layer is dried over anhydrous sodium sulfate
  4. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-152c9c9841ef4067891a61b3f95c33c8
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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