Hydrochloric Acid → 2-(2-Benzo[b]thiophen-5-ylethoxy)-1-ethanol

HRID 1007927Notes

Reaction equation

HRID 1007927 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][C:14](O)=[O:15])[CH:8]=[CH:9][C:2]1=2.B.[Na].C(OCC)(=O)C.Cl>O1CCCC1.O>[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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 219900582-(2-(1-Benzothiophene-5-yl)ethoxy)acetic acidHCID 178418435HCID 178418435, compound

Product 1

HCID 226665142-(2-Benzo[b]thiophen-5-ylethoxy)-1-ethanolYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 27 mL of tetrahydrofuran is dissolved 2.70 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-acetic acid. At an ice-cooled temperature, 0.65 g of sodium boron hydride is added to the solution, and stirred at the same temperature as above for 10 minutes. Then, at an ice-cooled temperature, 3.24 g of boron trifluoride diethyl ether complex is added to the reaction mixture over a period of 20 minutes, and the resulting mixture is stirred at the same temperature as above for 30 minutes and then at ambient temperature for 2 hours. The reaction mixture is introduced into a mixture of ethyl acetate and water, pH is adjusted to 1.0 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=3:1 to 2:1) to obtain 2.34 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-1-ethanol as an oily product.

Workup

  1. additionis added to the solution
  2. additionis added to the reaction mixture over a period of 20 minutes
  3. stirringthe resulting mixture is stirred at the same temperature as above for 30 minutes
  4. waitat ambient temperature for 2 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=3:1 to 2:1)

Sources & evidence

ORD record
ord-79de9110d0a74ffab355cdbf12e59b27
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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