Ethyl Acetate → HCID 14835698, compound

HRID 1709252Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[O:15][CH3:16].Br[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)P(=O)(N(C)C)N(C)C.[Cu]>[CH3:16][O:15][C:3]1[CH:4]=[C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][C:2]=1[O:1][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 160 °C

Procedure

6.67 g of ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate and 5.69 g of 3-bromopyridine were dissolved in 13.3 ml of hexamethyl phosphoric triamide. To the solution were added 4.15 g of potassium carbonate and 0.57 g of a copper powder. The mixture was stirred for 3 hours at 160° C. in a nitrogen atmosphere. The reaction mixture was mixed with 100 ml of ice water and 100 ml of ethyl acetate. The resulting insolubles were removed by filtration. An organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: benzene/ethyl acetate=10/1) to obtain 1.93 g of light yellow oily ethyl (E)-3-[3-methoxy-4-(3-pyridyloxy)phenyl]acrylate.

Workup

customThe resulting insolubles were removed by filtration
customAn organic layer was separated
washwashed with water
dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
customThe solvent was removed by distillation under reduced pressure
customThe residue was purified by a column chromatography (eluant: benzene/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-8cff6263ed6d41ed8def0e14194aa933
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948796

Reaction notes

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