Triethylamine → 2-(2-Thienyl)ethyl methanesulphonate

HRID 2255385Notes

Reaction equation

HRID 2255385 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]>C1COCC1>[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 chloride2×HCID 794002-Thiopheneethanol

Product 1

HCID 30477232-(2-Thienyl)ethyl methanesulphonateYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
5 °C

Procedure

To a flask was added 25.6 g. (0.20 mole) of 2-(2-thienyl)ethanol in 75 ml. of THF followed by 40.47 g. (0.40 mole) of triethylamine in 30 ml. of THF. The mixture was cooled to 5° C. and 34.4 g. (0.3 mole) of methanesulfonyl chloride in 20 ml. of THF was added dropwise over 20 minutes. The mixture exothermed to 20° C. and was kept at 20° C. during the methanesulfonyl chloride addition. An additional 150 ml. of THF was added to reduce the viscosity of the mixture after a precipitate had formed. After two hours, the reaction was quenched by the addition of 25 ml. of water which was followed by 25 ml of 10% aqueous hydrochloric acid and 200 ml. of ether. The ether layer was separated, washed with 50 ml. of 10% aqueous hydrochloric acid and twice with 75 ml. of saturated aqueous sodium bicarbonate solution, dried, and concentrated to give the 2-(2-thienyl)ethyl methanesulfonate, 38.0 g. (92.2% yield), as an oil.

Workup

  1. additionTo a flask was added 25.6 g
  2. customexothermed to 20° C.
  3. customhad formed
  4. customthe reaction was quenched by the addition of 25 ml
  5. customThe ether layer was separated
  6. washwashed with 50 ml
  7. dry with materialof saturated aqueous sodium bicarbonate solution, dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3d630f05d7c14ef8a7f68e4b8a084a4a
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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