Ethyl Acrylate → HCID 59555434, compound

HRID 1668530Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][OH:9])[N:3]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C(=O)(O)[O-].[Na+]>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:9][CH2:8][C:4]1[N:3]=[C:2](/[CH:12]=[CH:11]/[C:10]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Bromopyridine-6-methanol (2 g) was dissolved in 10 mL of dry DMF, and 1.73 mL of ethyl acrylate, 2.95 g of tetra(n-butyl)ammonium chloride, 1.78 g of sodium bicarbonate and 2 g of Molecular Sieves (Molecular Sieves 3A ( 1/16)) to the above solution, additionally under argon atmosphere 119 mg of palladium(II) acetate was added thereto, and then the mixture was stirred at 80° C. for 5 hours. After being cooled, the insoluble portion was filtrated off, and water was added thereto and then the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (hexane-ethyl acetate=2:1) to give 1.39 g of ethyl 3-(6-hydroxymethylpyridin-2-yl)-trans-acrylate as a light yellow oil.

Workup

temperatureAfter being cooled
filtrationthe insoluble portion was filtrated off
additionwater was added
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on silica gel (hexane-ethyl acetate=2:1)

Sources & evidence

ORD record: ord-c4f8aaa0a50e400ab118046a2e6e611b
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989446B2

Reaction notes

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