Water → Methyl (2E)-3-(5-methoxypyridin-3-yl)prop-2-enoate

HRID 45242

Reaction equation

[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(OCC)=O)C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=O)[CH:21]=[N:22][CH:23]=1.O>C1COCC1>[CH3:16][O:17][C:18]1[CH:19]=[C:20](/[CH:24]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH:21]=[N:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 3.12 g (78.1 mmol) of sodium hydride (60% in oil) in 30 mL of anhydrous THF is added, over 45 minutes, under argon and at 0° C., 16.4 g (78.1 mmol) of methyl (diethoxyphosphoryl)acetate in 10 mL of THF. Stirring is maintained for 30 minutes at 0° C. and 5.1 g (37.2 mmol) of 5-methoxypyridine-3-carbaldehyde in 20 mL of anhydrous THF are then added dropwise at 0° C. After cooling to room temperature, the reaction mixture is treated with 150 mL of water and then extracted with EtOAc (3×100 mL). The organic phases are combined, washed successively with water (2×20 mL), dried over Na2SO4, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAC gradient of 0 to 40% EtOAc. 1 g of methyl (2E)-3-(5-methoxypyridin-3-yl)prop-2-enoate is obtained in the form of a white powder.

Workup

additionis added, over 45 minutes, under argon and at 0° C.
temperatureAfter cooling to room temperature
extractionextracted with EtOAc (3×100 mL)
washwashed successively with water (2×20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue obtained
customis purified by chromatography on a column of silica gel
washeluting with a cyclohexane/EtOAC gradient of 0 to 40% EtOAc

Sources & evidence

ORD record: ord-3c00c64361cc4b72abed7773c1bb66fa
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541455B2

Linked notes

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