Methyl iodide → HCID 22033421, compound

HRID 1792320Notes

Reaction equation

[Li+].[CH3:2]C([N-]C(C)C)C.[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:27])[CH:16]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:17][O:18]2)=[CH:13][CH:12]=1.IC.[NH4+].[Cl-]>O1CCCC1>[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:27])[C:16]([CH3:2])([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:17][O:18]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of LDA (2.0 mol/l, 0.863 ml, 1.73 mmol) in tetrahydrofuran (1.5 ml) was added at −78° C. a solution of 7-methoxy-3-(4-pyridyl)chroman-4-one (220 mg, 0.863 mmol) in tetrahydrofuran (2 ml), which was then stirred for 30 minutes. Iodomethane (0.537 ml, 8.63 mmol) was added to -the reaclion solution, which was warmed to −10° C. and stirred for 3 hours. After the reaction was completed, the reaction solution was neutralized under ice-cooling using saturated aqueous NH4Cl solution, extracted with ethyl acetate, and washed with saturated saline solution. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=1:2) to give 7-methoxy-3-methyl-3-(4-pyridyl)chroman-4-one (131 mg, yield 56%).

Workup

stirringstirred for 3 hours
temperaturecooling
extractionextracted with ethyl acetate
washwashed with saturated saline solution
dry with materialThe organic layer was dried over magnesium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-58583feedb6c454f8356542d931ad6ea
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074819B2

Reaction notes

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