Diethyl Malonate → Diethyl 2-(6-Methoxy-3-pyridyl)malonate

HRID 747864Notes

Reaction equation

[H-].[Na+].Br[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1.[C:12]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>[Cu]Br>[CH2:17]([O:16][C:14](=[O:15])[CH:13]([C:4]1[CH:9]=[N:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)[C:12]([O:20][CH2:21][CH3:22])=[O:19])[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydride (60%, 36.2 mmoL, 1.45 g) was added into a solution of 5-bromo-2-methoxy-pyridine (16.5 mmoL, 2.13 mL), copper(I) bromide (32.9 mmoL, 4.72 g) and diethyl malonate (32.9 mmoL, 5.0 mL) in 1,4-dioxlane (20 mL) slowly at room temperature. After the addition, the resulting mixture was heated to 100° C. and stirred overnight. The mixture was then passed through a pad of Celite to remove brown solid. The filtrate was then concentrated in vacuo to afford a brown oil, which was then purified by column chromatography using hexanes:ethyl acetate (4:1˜2:1 ratio) as eluent to afford the title compound as a slight yellow oil.

Workup

additionAfter the addition
customto remove brown solid
concentrationThe filtrate was then concentrated in vacuo
customto afford a brown oil, which
customwas then purified by column chromatography

Sources & evidence

ORD record: ord-18cee5c5fd7b4f1280605df10669f44f
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399767B2

Reaction notes

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