Water → 3-(2-Methoxy-pyridin-4-yl)-acrylic acid methyl ester

HRID 474759Notes

Reaction equation

HRID 474759 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][N: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:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 27629962-Methoxypyridine-4-carbaldehyde

Product 1

HCID 677751253-(2-Methoxy-pyridin-4-yl)-acrylic acid methyl esterYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Methoxy-pyridine-4-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 2 hours. 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 50 g normal phase silica SNAP column and cyclohexane/EtOAc solvent system (gradient 2-20% of EtOAc in 20 column volumes). Solvent from the gathered fractions of appropriate composition was evaporated and obtained was 3-(2-methoxy-pyridin-4-yl)-acrylic acid methyl ester (1.3 g, yield=87.6%, purity=95%). MS: [M+H]+=194.14 1H NMR (300 MHz; CDCl3) δ/ppm 3.82(s, 3H), 3.95 (s, 3H), 6.54 (d, J=16.0 Hz, 1H), 6.80 (s, 1H), 6.97 (dd, J=5.38 Hz, J=1.31 Hz, 1H), 7.55 (d, J=16.0 Hz, 1H), 8.18 (d, J=5.38 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-82759857e554457c80264a0a2a12cc6b
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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