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Ethanethiol → 2-(4-Hydroxyphenyl)-3-[4-[2-(piperidin-1-yl)ethoxy]benzoyl]-6-hydroxybenzofuran

HRID 1955379
Notes
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Reaction equation

HRID 1955379 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:34]=[C:33]([O:35]C)[CH:32]=[CH:31][C:12]=3[C:13]=2[C:14](=[O:30])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[Cl-].[Cl-].[Cl-].[Al+3].C(S)C>C(Cl)CCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:34]=[C:33]([OH:35])[CH:32]=[CH:31][C:12]=3[C:13]=2[C:14](=[O:30])[C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[CH:19][CH:20]=2)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 9891548HCID 9891548, compound

Product 1

HCID 99557562-(4-Hydroxyphenyl)-3-[4-[2-(piperidin-1-yl)ethoxy]benzoyl]-6-hydroxybenzofuran

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title product was prepared by the demethylation of 2-(4-methoxyphenyl)-3-[4-[2-(piperidin-1-yl)ethoxy]benzoyl]-6-methoxybenzofuran, the product of Preparation 1a, supra. In a 250 ml three-neck round bottom flask were combined ethylene chloride (50 ml) and aluminum trichloride (9.60 g, 72 mmol) and ethanethiol (6.39 g, 103 mmol) to create a pale yellow liquid. To this liquid was then added the product of Example 1a(5.00 g, 10.3 mmol) in a gradual fashion. A red oil precipitated and the mixture was stirred for about 20 minutes. After cooling the reaction mixture in an ice bath 100 ml of tetrahydrofuran was added and the mixture was allowed to stir until all of the oil had gone into solution.

Workup

  1. customIn a 250 ml three-neck round bottom flask were combined
  2. customA red oil precipitated
  3. temperatureAfter cooling the reaction mixture in an ice bath 100 ml of tetrahydrofuran
  4. additionwas added
  5. stirringto stir until all of the oil

Sources & evidence

ORD record
ord-10133b3037614a7ab79cb27654d3ba5f
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06124311

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes