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

HRID 2390976Notes

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].[CH2:14]([N+](C)(C)C)[C:15]1[CH:20]=CC=CC=1.C(#N)C=C.Cl.[CH3:30][OH:31]>C1(C)C=CC=CC=1.O.O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:14][CH2:15][C:20]([O:31][CH3:30])=[O:13])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 7.5 °C

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 2.22 mL of acrylonitrile at 5° C., which was then stirred at 0 to 15° C. for 1.5 hours. To this reaction mixture were added 0.13 mL of hydrochloric acid, 10 mL of methanol and 1.52 g of water. Thereto was introduced 9.47 g of hydrogen chloride, which was then refluxed for 4 hours. After cooling, to the reaction mixture were added 15 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=5:1) to provide 7.36 g of methyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate as colorless oily form.

Workup

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

Sources & evidence

ORD record: ord-1ceb8775ffc7493e923227d8a20cfe02
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273902B2

Reaction notes

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