Hydrochloric Acid → 1-(Benzo[b]thiophen-5-yl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol

HRID 362988Notes

Reaction equation

HRID 362988 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH:10]([OH:16])[CH2:11][O:12][CH2:13][CH2:14][OH:15])[CH:8]=[CH:9][C:2]1=2.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl.C(OCC)C>N1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH:10]([OH:16])[CH2:11][O:12][CH2:13][CH2:14][O:15][S:23]([C:20]3[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[CH:8]=[CH:9][C:2]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 539187291-(Benzo[b]thiophen-5-yl)-2-(2-hydroxyethoxy)ethanol

Product 1

HCID 536544561-(Benzo[b]thiophen-5-yl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanolYield 51.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 54 ml of pyridine was dissolved 9.0 g of 1-(benzo[b]thiophen-5-yl)-2-(2-hydroxyethoxy)ethanol. To the solution was added, at -25° C., 7.2 g of p-toluenesulfonyl chloride. The mixture was allowed to stand at 0°-5° C. for 24 hours and further at room temperature for 4 hours. The reaction mixture was added to a mixture of 103 ml of 6N hydrochloric acid, 50 ml of ice water and 100 ml of diethyl ether. The resulting mixture was adjusted to pH 2.0 with 6N hydrochloric acid. The organic layer was separated. The aqueous layer was extracted with 30 ml of diethyl ether. The extract was combined with the previously separated organic layer. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=10/1) to obtain 7.7 g of colorless oily 1-(benzo[b]thiophen-5-yl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol.

Workup

  1. additionTo the solution was added, at -25° C.
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted with 30 ml of diethyl ether
  4. washThe combined organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-84db4f8c1e8e4a52b61b5e1bd2082468
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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