Water → 7-(Oxiran-2-yl)benzofuran

HRID 1199931Notes

Reaction equation

HRID 1199931 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[I-].[CH3:15][S+](C)(C)=O.O>CS(C)=O>[O:1]1[C:5]2[C:6]([CH:10]3[CH2:15][O:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 111264061-Benzofuran-7-carbaldehyde

Product 1

HCID 149589437-(Oxiran-2-yl)benzofuran

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of benzofuran-7-carboxaldehyde (4.4 g) in dry dimethylsulphoxide was added dropwise to a stirred solution of sodium hydride (60% dispersion in oil, 2.5 g) and trimethylsulphoxonium iodide (7.6 g) in dimethylsulphoxide (50 ml) at room temperature. After 1 hour iced water was added and extracted with diethylether. The extracts were washed with water, dried, filtered and evaporated to a yellow oil. Chromatography on silica eluting with 10:1:90 ether:triethylamine:hexane gave 7-benzofuranyl oxirane as an oil.

Workup

  1. extractionextracted with diethylether
  2. washThe extracts were washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated to a yellow oil

Sources & evidence

ORD record
ord-20790c38dd82409fbc481d8470754e26
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

Loading…