Hydrochloric Acid → HCID 21990147, compound

HRID 2377179Notes

Reaction equation

HRID 2377179 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][OH:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-].[K+].[C:15](#[N:18])[CH:16]=[CH2:17].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:17][CH2:16][C:15]#[N:18])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 14797Potassium HydroxideHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-ol

Product 1

HCID 21990147HCID 21990147, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To 2.00 g of 2-(1-benzothiophen-5-yl)-1-ethanol were added 13 mg of potassium hydroxide, 36 mg of tetra-n-butylammonium bromide and 1.11 mL of acrylonitrile, and the resulting mixture was stirred at 45° C. for 3 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 1 with 2 mol/L hydrochloric acid. The insoluble materials were removed and then the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; hexane:ethyl acetate=3:1) to obtain 2.46 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]propiono-nitrile as a colorless oil.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. customThe insoluble materials were removed
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by a column chromatography (eluent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0095d39e4fdb429cb8e598fe4bf98d78
Source dataset
uspto-grants-2008_12
Patent number
US07468443B2

Reaction notes

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