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

HRID 2085179Notes

Reaction equation

HRID 2085179 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-2f1b3bb52cf64831bcdd1d1e4e02e670
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

Loading…