m-Chloroperbenzoic acid → (2,3-Dihydro-2,4-dimethylbenzofuran-7-yl)diazenecarboxylic acid methyl ester
Reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[CH3:12][O:13][C:14]([NH:16][NH:17][C:18]1[C:26]2[O:25][CH:24]([CH3:27])[CH2:23][C:22]=2[C:21]([CH3:28])=[CH:20][CH:19]=1)=[O:15]>C(Cl)Cl>[CH3:12][O:13][C:14]([N:16]=[N:17][C:18]1[C:26]2[O:25][CH:24]([CH3:27])[CH2:23][C:22]=2[C:21]([CH3:28])=[CH:20][CH:19]=1)=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 37 °C
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.
Workup
- temperatureto cool to room temperature
- washwashed with 10% aqueous sodium carbonate solution
- customwater, then the liquid phases were separated
- dry with materialThe methylene chloride phase was dried (MgSO4)
- customthe solvent was evaporated
- customThe residue was crystallized from ether/hexane (1:1, v:v)
- customto give 1
Sources & evidence
- ORD record
- ord-f97a2e10c81c490db89bc271bf10bd2d
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04550121
Reaction notes
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