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

HRID 1411749Notes

Reaction equation

HRID 1411749 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-diazabicyclo[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-3dcb42c8502640d69097c32287b0a7be
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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