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

HRID 1376993Notes

Reaction equation

HRID 1376993 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-100c23bb239b4cd8a86a911d9a6ee0de
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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