4-Nitrobenzaldehyde → (3-Methoxymethoxypyridin-2-yl)-(4-nitrophenyl)methanol

HRID 565995Notes

Reaction equation

Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[Li].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]>C(OCC)C.CCCCCC.O1CCCC1.O>[CH3:11][O:10][CH2:9][O:8][C:7]1[C:2]([CH:25]([C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:28][CH:27]=2)[OH:26])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Under nitrogen atmosphere, to a solution of 2-bromo-3-methoxymethoxypyridine (10.00 g) in diethylether (150 ml) was added a solution of n-butyllithium in hexane (1.6M, 31.5 ml) at −78° C., and the mixture was stirred for 1 hour to prepare the lithium salt. The resulting lithium salt was dropwise added to a solution of 4-nitrobenzaldehyde (6.93 g) in tetrahydrofuran (100ml) cooled at −78° C., and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture was added water to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:3→1:2) to give (3-methoxymethoxypyridin-2-yl)-(4-nitrophenyl)methanol (11.78 g) as yellow oil.

Workup

stirringthe mixture was stirred at the same temperature for 3 hours
customthe reaction
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated sodium chloride solution
dry with materialdried with magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was separated
custompurified with column chromatography (ethyl acetate/hexane=1:3→1:2)

Sources & evidence

ORD record: ord-d2339b6d007049929d293c0daf49ef5e
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172061B2

Reaction notes

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