m-Chloroperbenzoic acid → (3,4-Dihydro-2,5-dimethyl-2H-1-benzopyran-8-yl)diazenecarboxylic acid methyl ester

HRID 637632Notes

Reaction equation

[CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][CH:13]1[CH2:18][CH2:17][C:16]2[C:19]([CH3:28])=[CH:20][CH:21]=[C:22]([NH:23][NH:24][C:25]([OH:27])=[O:26])[C:15]=2[O:14]1>C(Cl)Cl>[CH3:1][O:26][C:25]([N:24]=[N:23][C:22]1[C:15]2[O:14][CH:13]([CH3:12])[CH2:18][CH2:17][C:16]=2[C:19]([CH3:28])=[CH:20][CH:21]=1)=[O:27]

Participants

Conditions

Temperature: 35 °C

Procedure

A solution of 13.8 g of MCPBA in 100 ml of methylene chloride was added drop-by-drop over 10 minutes to a stirred solution of 16.1 g of 1G in 150 ml of methylene chloride at room temperature. The resulting mixture was stirred and refluxed (35° C.) for 30 minutes, then washed with 10% aqueous sodium carbonate solution. The resulting methylene chloride solution was dried (MgSO4), and the solvent was evaporated. The residue was purified by column chromatography over silica gel, using a 1:4:20 v:v:v mixture of THF, ethyl acetate and hexane as eluent, to give 1, as a brick red solid, m.p.: 95°-97° C.

Workup

washwashed with 10% aqueous sodium carbonate solution
dry with materialThe resulting methylene chloride solution was dried (MgSO4)
customthe solvent was evaporated
customThe residue was purified by column chromatography over silica gel
additionv:v mixture of THF, ethyl acetate and hexane as eluent
customto give 1

Sources & evidence

ORD record: ord-72839abe6f764d64a8c1fde35a726db6
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04558040

Reaction notes

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