Sodium Thiosulfate → 5-Acetoxy-4,6-di-tert-butylbenzofuran

HRID 1900520Notes

Reaction equation

HRID 1900520 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([O:15][CH3:16])=[C:7](CC=O)[C:6]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:3])[CH3:2].[CH3:24][Si](I)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:9][C:8]2[O:15][CH:16]=[CH:24][C:7]=2[C:6]=1[C:20]([CH3:21])([CH3:23])[CH3:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 108817494-Acetoxy-3,5-di-tert-butyl-2-formylmethylanisole

Product 1

HCID 118223325-Acetoxy-4,6-di-tert-butylbenzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Acetoxy-3,5-di-tert-butyl-2-formylmethylanisole (16 g) was dissolved in dichloromethane (100 ml) and trimethylsilyl iodide (7.1 ml) was added dropwise to the solution under cooling with ice. After stirring the mixture at room temperature for 1 h, a saturated aqueous solution of sodium thiosulfate was added and the mixture was subjected to extraction with chloroform. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butylbenzofuran quantitatively (14.3 g) as a white solid.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe mixture was subjected to extraction with chloroform
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-8f98a1a670ed44c4a33582b8a96dac66
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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