Hydrochloric Acid → HCID 21962589, compound

HRID 1007947Notes

Reaction equation

HRID 1007947 reaction equation
B.[Na].[S:3]1[CH:7]=[CH:6][C:5]2[C:8]([CH2:12][CH:13]=[O:14])=[CH:9][CH:10]=[CH:11][C:4]1=2.O.Cl>CO.C(OCC)(=O)C>[S:3]1[CH:7]=[CH:6][C:5]2[C:8]([CH2:12][CH2:13][OH:14])=[CH:9][CH:10]=[CH:11][C:4]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 22666290HCID 22666290, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 21962589HCID 21962589, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In 8 mL of 90% methanol is suspended 0.16 g of sodium boron hydride. At an ice-cooled temperature, a solution of 1.45 g of 2-benzo[b]thiophen-4-ylacetaldehyde in 6 mL of methanol is dropwise added to the suspension obtained above, and the resulting mixture is stirred at ambient temperature for 30 minutes. Water and ethyl acetate are added to the reaction mixture, pH is adjusted to 2.0 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: toluene:ethyl acetate=50:1 to 2:1) to obtain 0.88 g of 2-benzo[b]-thiophen-4-yl-1-ethanol.

Workup

  1. customobtained above, and the resulting mixture
  2. customthe organic layer is separated
  3. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customthe residue is purified by column chromatography (eluent: toluene:ethyl acetate=50:1 to 2:1)

Sources & evidence

ORD record
ord-f2521a88a07c412aa532d671175d7022
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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