Water → 5-{4-[Chloro(cyclohexyl)methyl]-5-(methoxymethyl)furan-2-yl}-2-methoxypyridine

HRID 1877089Notes

Reaction equation

[CH:1]1([CH:7]([C:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[O:11][C:10]=2[CH2:22][O:23][CH3:24])O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:27])=O.N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[Cl:27][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[N:16][CH:15]=2)[O:11][C:10]=1[CH2:22][O:23][CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of cyclohexyl[2-(methoxymethyl)-5-(6-methoxypyridin-3-yl)furan-3-yl]methanol (0.8 g) in toluene (10 mL) were added thionyl chloride (0.2 mL) and pyridine (0.3 mL) at 0° C., and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (0.8 g, 100%) as an oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-66fd55bace88448cb250955a264a36b2
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309580B2

Reaction notes

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