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

HRID 553219Notes

Reaction equation

HRID 553219 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-:13].C([N+](C)(C)C)[C:15]1[CH:20]=[CH:19][CH:18]=CC=1.[C:25](#N)[CH:26]=[CH2:27].Cl.S(=O)(=O)(O)O.[OH2:35]>C(O)CCC.O1CCCC1.C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:27][CH2:26][C:25]([O:35][CH2:18][CH2:19][CH2:20][CH3:15])=[O:13])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

10

Reactant 6

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

Product 1

HCID 57615037Butyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To toluene (5 mL) suspension of 5.00 g of 2-(1-benzothiophen-5-yl)ethanol were added 0.23 g of 40% (w/w) benzyltrimethylammonium hydroxide aqueous solution and 2.28 mL of tetrahydrofuran, and dropwise added 2.20 mL of acrylonitrile at 0 to 10° C., which was then stirred at same temperature for 1.5 hours. To this reaction mixture were added 0.1 mL of hydrochloric acid, 10 mL of butanol and 5 mL of 50% (w/w) sulfuric acid, which was then refluxed for 15 hours. After cooling, to the reaction mixture was added 15 mL of water. 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=10:1) to provide 6.65 g of butyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate as colorless oily form.

Workup

  1. temperaturewas then refluxed for 15 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-37271d63149b4aaf869acaab8b71975a
Source dataset
uspto-grants-2011_05
Patent number
US07951963B2

Reaction notes

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