Benzyl Bromide → Diethyl 4-(benzyloxy)pyridine-2,6-dicarboxylate

HRID 870282Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:7]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[CH2:24]([O:12][C:10]1[CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 82 °C

Procedure

To a solution of 4 (6.88 g, 28 mmol) in acetonitrile and K2CO3 (6.31 g, 45 mmol) was carefully added benzyl bromide (3.34 mL, 27 mmol). The resulting solution was stirred at 82° C. under reflux overnight. The reaction was stopped by filtration of K2CO3 and the solvent was removed under reduced pressure. The solid obtained was recrystallized from hot hexanes to yield 96% of the product as a white solid.

Workup

temperatureunder reflux overnight
filtrationThe reaction was stopped by filtration of K2CO3
customthe solvent was removed under reduced pressure
customThe solid obtained
customwas recrystallized from hot hexanes

Sources & evidence

ORD record: ord-479842ad3242468f9cee903bd35a50ba
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969549B2

Reaction notes

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