Hydrochloric Acid → 2-(1-Benzothiophen-5-yl)ethan-1-ol

HRID 2390970Notes

Reaction equation

HRID 2390970 reaction equation
[BH4-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][C:13](O)=[O:14])=[CH:11][C:6]=2[CH:5]=[CH:4]1.Cl.COCCOC.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.O.CC(C)=O.COCCOC>[S:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][OH:14])=[CH:11][C:6]=2[CH:5]=[CH:4]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 11469582Benzo[b]thiophene-5-acetic acidHCID 86628724Hydrochloride 1,2-dimethoxyethane

Product 1

HCID 119833712-(1-Benzothiophen-5-yl)ethan-1-olYield 84.6%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To 5 mL of 1,2-dimethoxyethane was suspended 2.95 g of sodium borohydride, to which were dropwise added 1,2-dimethoxyethane (25 mL) solution of 10 g of (1-benzothiophen-5-yl)acetic acid, and 11 mL of 6.9 mol/L hydrochloride/1,2-dimethoxyethane solution, which was then stirred at room temperature for 1 hour. To this reaction mixture was dropwise added 5 mL of acetone, which was then stirred for 30 minutes. Thereto were added 20 mL of water, 30 mL of toluene and 2 mL of 2 mol/L hydrochloric acid. Next, after the pH was adjusted to 9.5 with 20 mL of 2 mol/L sodium hydroxide aqueous solution, the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, followed by distilling off the solvent. Thereto were added cyclohexane and toluene. The precipitate was collected by filtration to provide 7.84 g of 2-(1-benzothiophen-5-yl)ethanol as white solid form.

Workup

  1. stirringwas then stirred for 30 minutes
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent
  5. additionThereto were added cyclohexane and toluene
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-86f68d1aa9ad4e04b4be03c0f716db64
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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