m-Chloroperbenzoic acid → N-(7-chloro-2,3-dihydro-2-(hydroxymethyl)-4-benzofuranyl)-3,4,5,6-tetrahydrophthalimide

HRID 344593Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:15]1[C:20]([OH:21])=[C:19]([Cl:22])[CH:18]=[CH:17][C:16]=1[N:23]1[C:27](=[O:28])[C:26]2[CH2:29][CH2:30][CH2:31][CH2:32][C:25]=2[C:24]1=[O:33])[CH:13]=[CH2:14]>ClCCCl>[Cl:22][C:19]1[C:20]2[O:21][CH:13]([CH2:14][OH:9])[CH2:12][C:15]=2[C:16]([N:23]2[C:27](=[O:28])[C:26]3[CH2:29][CH2:30][CH2:31][CH2:32][C:25]=3[C:24]2=[O:33])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 1.50 g of 80% m-chloroperbenzoic acid (MCPBA) in 20 mL of 1,2-dichloroethane was added dropwise to a solution of 2.0 g of 3D in 25 mL of 1,2-dichloroethane at room temperature. The resulting mixture was heated at 70° C. for four hours, cooled and extracted with saturated aqueous sodium sulfite solution, until no reaction to starch/iodide paper occurred. The organic phase was separated, washed with saturated aqueous sodium bicarbonate solution, water, brine, dried (Na2SO4) and stripped of solvent. The residue was flash chromatographed over silica gel, with a 2:3 v:v mixture of ethyl acetate and hexane as eluent, to obtain the title compound, as yellow crystals, m.p.: 193°-195° C.

Workup

temperaturecooled
extractionextracted with saturated aqueous sodium sulfite solution, until no reaction to starch/iodide paper
customThe organic phase was separated
washwashed with saturated aqueous sodium bicarbonate solution, water, brine
dry with materialdried (Na2SO4)
customchromatographed over silica gel, with a 2:3 v
additionv mixture of ethyl acetate and hexane as eluent

Sources & evidence

ORD record: ord-9e2734b03a5c48efa367b67f1b5871c9
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053071

Reaction notes

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