2-Methanesulfonyloxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one → 2-Iodomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900719

Reaction equation

CS(O[CH2:6][CH:7]1[O:21][C:10]2=[C:11]3[C:16](=[C:17]([CH3:19])[CH:18]=[C:9]2[CH2:8]1)[NH:15][C:14](=[O:20])[CH:13]=[CH:12]3)(=O)=O.[I:22]([O-])(=O)=O.[Na+]>CN(C)C=O>[I:22][CH2:6][CH:7]1[O:21][C:10]2=[C:11]3[C:16](=[C:17]([CH3:19])[CH:18]=[C:9]2[CH2:8]1)[NH:15][C:14](=[O:20])[CH:13]=[CH:12]3

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-methanesulfonyloxymethyl-5-methyl -2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (931 mg) in dimethylformamide (20 ml), sodium iodate (4.5 g) was added, and the mixture was stirred at 100° C. for 2 hours. After completion of the reaction, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent: chloroform) to obtain 1 g (assayed quantitatively) of the target compound as a light yellow powder.

Workup

customAfter completion of the reaction
distillationthe solvent was distilled off
customthe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record: ord-070d70ff3d7840d5bf4cd059e38e424e
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Linked notes

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