Reaction #552206

Reaction equation

m-chloroperoxybenzoic acid

1F

2-(2,3-dihydro-2,4-dimethylbenzofuran-7-yl)hydrazinecarboxylic acid methyl ester

→

(2,3-dihydro-2,4-dimethylbenzofuran-7-yl)diazenecarboxylic acid methyl ester

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Temperatureto cool to room temperature
2. 2
   Washwashed with 10% aqueous sodium carbonate solution
3. 3
   Otherwater, then the liquid phases were separated
4. 4
   DryingThe methylene chloride phase was dried (MgSO4)
5. 5
   Otherthe solvent was evaporated
6. 6
   OtherThe residue was crystallized from ether/hexane (1:1, v:v)
7. 7
   Otherto give 1

Procedure

A solution of 5.3 g of 85% m-chloroperoxybenzoic acid (MCPBA) in 100 ml of methylene chloride was added slowly to a solution of 6.2 g of 1F in 100 ml of methylene chloride, at room temperature. The mixture warmed to about 37° C. It was allowed to cool to room temperature, let stand for 18 hours, washed with 10% aqueous sodium carbonate solution, then water, then the liquid phases were separated. The methylene chloride phase was dried (MgSO4) and the solvent was evaporated. The residue was crystallized from ether/hexane (1:1, v:v) to give 1, as an orange solid, m.p.: 62°-65° C.

Source