Water → 4-Methoxy-2-(trimethylstannyl)benzo(b)furan

HRID 460607Notes

Reaction equation

HRID 460607 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[CH:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[CH3:17][Sn:18](Cl)([CH3:20])[CH3:19].O>C1COCC1>[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([Sn:18]([CH3:20])([CH3:19])[CH3:17])[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Procedure

To a solution of 4-methoxybenzo(b)furan (2.50 g) in THF (50 ml) was added n-butyllithium (1.54 M hexane solution) (16.5 ml) at −78° C. and the mixture was stirred at the same temperature for 20 min. To this solution was added trimethyltin chloride (5.00 g) and the mixture was further stirred at the same temperature for 1 hr. The reaction mixture was warmed to room temperature and water (200 ml) was added. The mixture was extracted with ethyl acetate, and the obtained organic layer was washed with water and saturated brine and dried over magnesium sulfate. This solution was concentrated under reduced pressure to give the title compound (5.86 g) as pale-yellow crystals.

Workup

  1. stirringthe mixture was further stirred at the same temperature for 1 hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe obtained organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThis solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f6cb05b37acf44a9996784c8dce6278f
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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