Sulfur Dioxide → HCID 23690620, compound

HRID 730214Notes

Reaction equation

HRID 730214 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Li:10]CCCC.[S:15](=[O:17])=[O:16]>C1COCC1.CCCCCC>[Li+:10].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:15]([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 1119Sulfur DioxideHCID 9223BenzofuranHCID 178418339Butyllithium

Product 1

HCID 23690620HCID 23690620, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of benzofuran (10 mmol) in dry THF (15 mL) at −40° C., n-BuLi (2.5 M in hexanes; 4.4 mL; 11 mmol) was added dropwise. The reaction mixture was stirred at −40° C. for 30-40 min. Sulfur dioxide gas was passed into the reaction mixture, keeping the tip of the needle just above the reaction mixture, for about 5-10 min. A white precipitate was formed. The reaction mixture was then brought to RT and the stirring was continued for 1 h, then the mixture was diluted with hexane (20 mL) to give benzofuran-2-sulfinic acid lithium salt as a white precipitate. The solid was filtered and dried in vacuo to afford the salt.

Workup

  1. waitfor about 5-10 min
  2. customA white precipitate was formed
  3. customwas then brought to RT
  4. waitthe stirring was continued for 1 h

Sources & evidence

ORD record
ord-114246f8bf1a463b903f9e5ef8b72a4f
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

Loading…