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

HRID 553215Notes

Reaction equation

HRID 553215 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-e9b2e82a5c4d440282131279363fa2c8
Source dataset
uspto-grants-2011_05
Patent number
US07951963B2

Reaction notes

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