Hydrochloric Acid → 4-Methoxy-3-(2-phenylethyl)benzo[b]thiophene

HRID 230884Notes

Reaction equation

HRID 230884 reaction equation
C([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:6]=2[C:5]=1[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(O)=O.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:14][O:13][C:12]1[C:6]2[C:5]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:4][S:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 231035202-Carboxy-4-methoxy-3-(2-phenylethyl)benzo[b]thiophene

Product 1

HCID 231035114-Methoxy-3-(2-phenylethyl)benzo[b]thiopheneYield 89.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

A suspension of 2-carboxy-4-methoxy-3-(2-phenylethyl)benzo[b]thiophene (1 g) and a catalytic amount of copper powder in quinoline (15 mL) was stirred at 200° C. for 2 hours. The reaction mixture was cooled to room temperature and poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1) to give the title compound (0.77 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with 1 mol/L hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-50415b8d3c7d4c0d81ff32d21763ee6f
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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