Water → 7-(4-Methylbenzyl)benzo[b]thiophene

HRID 15409Notes

Reaction equation

HRID 15409 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.[S:8]1[CH:12]=[CH:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:16]([CH:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)O)[C:9]1=2.O>C(#N)C>[CH3:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:17][C:16]2[C:9]3[S:8][CH:12]=[CH:11][C:10]=3[CH:13]=[CH:14][CH:15]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 68717781Benzo[b]thiophen-7-yl-p-tolylmethanol

Product 1

HCID 670691007-(4-Methylbenzyl)benzo[b]thiopheneYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of sodium iodide (2.0 g) in acetonitrile was added chlorotrimethylsilane (1.5 g) at room temperature. After the mixture was stirred at room temperature for 15 minutes, benzo[b]thiophen-7-yl-p-tolylmethanol (0.68 g) was added to the mixture, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was poured into water, and the mixture was extracted with hexane. The organic layer washed with water and brine 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) to give the title compound (0.57 g) as colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. extractionthe mixture was extracted with hexane
  3. washThe organic layer 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)

Sources & evidence

ORD record
ord-ba1270ebd64c429686d97f9ef417a6f9
Source dataset
uspto-grants-2010_06
Patent number
US07732596B2

Reaction notes

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