Water → Methyl beta-(2-methoxypyridin-5-yl)acrylate

HRID 474754Notes

Reaction equation

HRID 474754 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.[CH3:11][O:12][C:13]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:14].O>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:14])[CH:15]=[CH:9][C:6]1[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 53929170Methyl beta-(2-methoxypyridin-5-yl)acrylateYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxy-pyridine-3-carbaldehyde (1 g, 7.29 mmol, 1 eq) in 50 ml of dry DCM was added portionwise (methoxycarbonylmethylene)triphenylphosphorane (1.05 eq, 2.56 g). The mixture was stirred at room temperature for 16 hours (overnight). The mixture was then poured into 200 ml of water and the organic substances were extracted with DCM (twice, 150 ml of DCM was used in total) The gathered DCM layers were dried and the resulting crude was purified by chromatography on BIOTAGE SP1 purification device using 100 g normal phase silica SNAP column and cyclohexane/EtOAc solvent system (gradient 3-22% of EtOAc in 20 column volumes). Solvent from the gathered fractions of appropriate composition was evaporated and obtained was 3-(6-methoxy-pyridin-3-yl)-acrylic acid methyl ester (1.04 g, yield=73.8%, purity=95%). MS: [M+H]+=194.17 1H NMR (300 MHz; CDCl3) δ/ppm 3.81 (s, 3H), 3.97 (s, 3H), 6.34 (d, J=16.02 Hz, 1H), 6.77 (d, J=8.79 Hz, 1H), 7.65 (d, J=16.02 Hz, 1H), 7.77 (dd, J=8.70 Hz, J=2.40 Hz, 1H), 8.27 (d, J=2.40 Hz, 1H)

Workup

  1. extractionthe organic substances were extracted with DCM (twice, 150 ml of DCM
  2. customwere dried
  3. customthe resulting crude was purified by chromatography on BIOTAGE SP1 purification device
  4. customSolvent from the gathered fractions of appropriate composition was evaporated
  5. customobtained

Sources & evidence

ORD record
ord-db7f964a7f184dfb81893e889b8e545b
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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