Methyl Acrylate → HCID 67775705, compound

HRID 474752Notes

Reaction equation

HRID 474752 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.C1N2CCN(CC2)C1.[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].O1CCOCC1>[Cl-].[Na+].O.O>[CH3:23][O:22][C:18](=[O:21])[C:19]([CH:8]([OH:9])[C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[CH2:20]

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 9237DabcoHCID 312751,4-DioxaneHCID 101925666-Methyl-3-pyridinecarboxaldehyde

Product 1

HCID 67775705HCID 67775705, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 6-methylpyridine-3-carboxaldehyde, 97% (500 mg, 4.0 mmol, 1 eq), DABCO (458 mg, 1 eq) and methyl acrylate (1.80 ml, 5 eq) in a 1,4-dioxane (20 ml)/water (20 ml) solvent mixture was stirred at room temperature for 4 days. The resulting mixture was poured in 150 ml of brine and the organics were extracted with DCM (3×300 ml). The gathered DCM layers were dried, solvent was evaporated and the obtained crude was purified by chromatography on Biotage SP1 purification device using 25 g normal phase silica SNAP column and DCM/MeOH solvent system (gradient 1-6% of MeOH in 20 CV). Solvent from gathered fractions of appropriate composition was evaporated and the resulting crude was triturated with cyclohexane to obtain 2-[hydroxy-(6-methyl-pyridin-3-yl)-methyl]-acrylic acid methyl ester in form of white powder (375 mg, yield=43.8%, purity=95%). MS: [M+H]+=208.17 1H NMR (300 MHz; CDCl3) δ/ppm 2.55 (s, 3H), 3.11 (d, J=5.86 Hz, 1H), 3.74 (s, 3H), 5.58 (d, J=5.58 Hz, 1H), 5.87 (s, 1H), 6.38 (s, 1H), 7.15 (d, J=8.13 Hz, 1H), 7.61 (dd, J=8.13 Hz, J=2.45 Hz, 1H), 8.48 (d, J=2.45 Hz, 1H)

Workup

  1. extractionthe organics were extracted with DCM (3×300 ml)
  2. dry with materialThe gathered DCM layers were dried
  3. customsolvent was evaporated
  4. customthe obtained crude
  5. customwas purified by chromatography on Biotage SP1 purification device
  6. customwas evaporated
  7. customthe resulting crude was triturated with cyclohexane

Sources & evidence

ORD record
ord-bdc268f9137e44d6a6943d0e036e0804
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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