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

HRID 705995Notes

Reaction equation

HRID 705995 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 coloumn and cyclohexane/EtOAc solvent system (gradient 2-20% of EtOAc in 20 coloumn 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-f822eaf9b9da4a2884a7e7c877d2684a
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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