Hydrochloric Acid → 2-(2-Benzo[b]thiophen-5-ylethoxy)ethyl methanesulfonate

HRID 1007928Notes

Reaction equation

HRID 1007928 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][OH:15])[CH:8]=[CH:9][C:2]1=2.[CH3:16][S:17](Cl)(=[O:19])=[O:18].N1C=CC=CC=1.Cl>C(Cl)Cl.O>[CH3:16][S:17]([O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:2]2[S:1][CH:5]=[CH:4][C:3]=2[CH:6]=1)(=[O:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 226665142-(2-Benzo[b]thiophen-5-ylethoxy)-1-ethanol

Product 1

HCID 219900502-(2-Benzo[b]thiophen-5-ylethoxy)ethyl methanesulfonateYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In 20 mL of methylene chloride is dissolved 2.10 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-1-ethanol. At an ice-cooled temperature, 1.63 g of methanesulfonyl chloride and 1.47 g of pyridine are added to the solution obtained above, and the mixture thus formed is stirred at the same temperature as above for 30 minutes and then at ambient temperature for 12 hours. Then, methylene chloride and water are added to the reaction mixture, pH is adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: n-hexane:ethyl acetate=4:1 to 2:1) to obtain 2.50 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-ethyl methanesulfonate.

Workup

  1. additionare added to the solution
  2. customobtained above, and the mixture
  3. customthus formed
  4. waitat ambient temperature for 12 hours
  5. customthe organic layer is separated
  6. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. customthe residue is purified by column chromatography (eluent: n-hexane:ethyl acetate=4:1 to 2:1)

Sources & evidence

ORD record
ord-795dc92c2639438599d34baaaf2ed9e5
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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