Hydrochloric Acid → 4-(2-Phenylethyl)benzo[b]thiophene

HRID 15405

Reaction equation

HRID 15405 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[C:17]3[CH:16]=[CH:15][S:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.O>O1CCCC1>[C:1]1([CH2:7][CH2:8][C:9]2[C:17]3[CH:16]=[CH:15][S:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 231567054-[(E)-2-Phenylvinyl]benzo[b]thiophene

Product 1

HCID 687176824-(2-Phenylethyl)benzo[b]thiopheneYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(E)-2-phenylvinyl]benzo[b]thiophene (0.56 g) and triethyl amine (2.63 mL) in tetrahydrofuran (25 mL) was added 2,4,6-triisopropylbenzenesulfonylhydrazide (5 g), and the mixture was refluxed overnight under an argon atmosphere. After the reaction mixture was cooled to room temperature, 2 mol/L hydrochloric acid was added to the mixture, and the mixture was stirred for 10 minutes. The mixture was poured into water, and the mixture was extracted with diethyl ether. The extract was washed with water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane) to give a mixture of the starting material and the title compound (0.43 g). This mixture was dissolved in triethylamine (2.04 g) and tetrahydrofuran (18 mL), and 2,4,6-triisopropylbenzenesulfonylhydrazide (3.28 g) was added to the solution, and the mixture was refluxed overnight under an argon atmosphere. The reaction mixture was cooled to room temperature and 2 mol/L hydrochloric acid was added to the mixture, and the mixture was stirred for 10 minutes. The mixture was poured into water, and the mixture was extracted with diethyl ether. The extract washed with water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane) to give the title compound (0.4 g).

Workup

  1. temperaturethe mixture was refluxed overnight under an argon atmosphere
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane)
  7. customto give
  8. additiona mixture of the starting material

Sources & evidence

ORD record
ord-e0fe9971618743f78c249e07e860e8ac
Source dataset
uspto-grants-2010_06
Patent number
US07732596B2

Linked notes

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