Hydrochloric Acid → Propyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate

HRID 2390972Notes

Reaction equation

HRID 2390972 reaction equation
[OH-:1].C([N+](C)(C)C)[C:3]1[CH:8]=[CH:7]C=CC=1.[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH2:22][CH2:23][OH:24])=[CH:21][C:16]=2[CH:15]=[CH:14]1.[C:25](#N)[CH:26]=[CH2:27].Cl.S(=O)(=O)(O)O.[OH2:35]>C1(C)C=CC=CC=1.C(O)CC>[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH2:22][CH2:23][O:24][CH2:27][CH2:26][C:25]([O:35][CH2:7][CH2:8][CH3:3])=[O:1])=[CH:21][C:16]=2[CH:15]=[CH:14]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-ol

Product 1

HCID 57615042Propyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
10 °C

Procedure

To toluene (5 mL) suspension of 0.23 g of 40% (w/w) benzyltrimethylammonium hydroxide aqueous solution was added 5.00 g of 2-(1-benzothiophen-5-yl)ethanol, and dropwise added 2.20 mL of acrylonitrile at 0 to 5° C., which was then stirred at 0 to 20° C. for 1 hour. To this reaction mixture was added 0.125 mL of hydrochloric acid. Thereto were added 10 mL of propanol, 1.0 mL of water and 3.1 mL of sulfuric acid, which was then refluxed for 6.5 hours. After cooling, to the reaction mixture were added 10 mL of water and 10 mL of toluene. The organic layer was separated, and dried over anhydrous magnesium sulfate. After insoluble matter was filtered off, the solvent was distilled off under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=15:1 to 7:1) to provide 7.21 g of propyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate as colorless oily form.

Workup

  1. temperaturewas then refluxed for 6.5 hours
  2. temperatureAfter cooling, to the reaction mixture
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter insoluble matter was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified

Sources & evidence

ORD record
ord-ffa0ea236d3d4598a27adf0424a1b0a1
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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