Methyl iodide → HCID 86645943, compound

HRID 1095874Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)=[O:12].[H-].[Na+].[CH3:22]I>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:22])[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)=[O:12]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-(2-chloro-4-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-ethanone (17.1 g, 0.058 mol) in tetrahydrofuran (550 ml) was added sodium hydride (55%-65% dispersion in mineral oil, 2.43 g, 0.063 mol). The mixture was stirred at 45° C. for 3 h and then placed in an ice bath. A solution of methyl iodide (9.01 g, 0.0635 mol) in tetrahydrofuran (50 ml) was added dropwise. The ice bath was removed and the mixture was stirred at 35° C. for 3 h. The mixture was poured in ice water and extracted twice with AcOEt. The organic phases were washed with brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography (silica gel, heptane/AcOEt 4:1) to give the title compound (14.7 g) as yellow viscous oil. MS (m/e, ISP neg. ion)=310.3 [M−H−].

Workup

customplaced in an ice bath
customThe ice bath was removed
stirringthe mixture was stirred at 35° C. for 3 h
additionThe mixture was poured in ice water
extractionextracted twice with AcOEt
washThe organic phases were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by column chromatography (silica gel, heptane/AcOEt 4:1)

Sources & evidence

ORD record: ord-4e5e0108d250444391390e3e0f61c64f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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