Triethylamine → 2-(2-Thienyl)ethyl methanesulphonate

HRID 2210804Notes

Reaction equation

HRID 2210804 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 794002-Thiopheneethanol

Product 1

HCID 30477232-(2-Thienyl)ethyl methanesulphonateYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (0° C.) mixture of 13 g of 2-thiopheneethanol and 15.3 g of N,N-diethylethanamine in 90 ml of dichloromethane there were added dropwise 8.6 ml of methanesulfonyl chloride. Stirring was continued for 1/2 hour and then the reaction mixture was washed with ice-water, dried, filtered and evaporated. The residue was taken up in 2,2'-oxybispropane and the whole was evaporated again, yielding 20 g (95.7%) of 2-thiopheneethanol methanesulfonate (ester) (interm. 9);

Workup

  1. temperaturecooled
  2. stirringStirring
  3. washthe reaction mixture was washed with ice-water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customthe whole was evaporated again

Sources & evidence

ORD record
ord-fa682cb8b5fc46a29ff8b51a3e256193
Source dataset
uspto-grants-1995_10
Patent number
US05461050

Reaction notes

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