Methyl Acrylate → Methyl beta-hydroxy-alpha-methylene-2-pyridinepropanoate

HRID 1021879Notes

Reaction equation

HRID 1021879 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11]>N12CCN(CC1)CC2.C(Cl)(Cl)Cl>[OH:8][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10](=[CH2:11])[C:9]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 11008779Methyl beta-hydroxy-alpha-methylene-2-pyridinepropanoateYield 60%

Reagents, catalysts & solvents 2

HCID 9237DabcoCatalystHCID 6212ChloroformSolvent

Procedure

A 250-mL single-neck round-bottomed flask was charged with chloroform (100 mL), picolinaldehyde (10.7 g, 0.10 mol), methyl acrylate (8.60 g, 0.10 mol), and 1,4-diaza-bicyclo[2.2.2]octane (0.560 g, 5.00 mmol). The reaction mixture stirred at room temperature for 48 h. After this time the reaction was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 3:1 petroleum ether/ethyl acetate to afford 193a as dark yellow oil (11.6 g, 60%). MS-ESI: (M+H)+ 194.2. 1H NMR (500 MHz, CDCl3) δ 8.54 (d, J=5.0 Hz, 1H), 7.69-7.66 (m, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.22-7.20 (m, 1H), 6.36 (s, 1H), 5.97 (s, 1H), 5.62 (s, 1H), 4.85 (s, 1H), 3.74 (s, 3H).

Workup

  1. concentrationAfter this time the reaction was concentrated under reduced pressure
  2. customthe residue was purified by silica-gel column chromatography
  3. washeluting with 3:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-bbd646cef78e47e7bcddf749c160d065
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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