Ethanol → HCID 87106032, compound

HRID 922306Notes

Reaction equation

HRID 922306 reaction equation
O=[C:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([CH2:9][O:10][C:11]2[N:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[N:32]1C=CC=CC=1.C[CH2:39][OH:40]>>[CH3:39][O:40]/[N:32]=[C:2](/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)\[CH2:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([CH2:9][O:10][C:11]2[N:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1049PyridineHCID 86695786HCID 86695786, compound

Product 1

HCID 87106032HCID 87106032, compoundYield 23%

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl (2E)-3-(6-{[4-(2-oxo-2-phenylethoxy)benzyl]oxy}pyridin-3-yl)prop-2-enoate (0.13 g, 0.3 mmol) in ethanol was added pyridine (0.038 g, 0.45 mmol) and O-Methoxylamine hydrochloride, the resulting mass was refluxed at 80° C. for 3 h. Reaction quenched with water and extracted with ethyl acetate, organic layer was washed with water and brine solution dried over anhydrous Na2SO4 and concentrated to colourless oil (0.03 g, Yield: 23%); MS (ESI, 120 eV): m/z=449 (M+H)+.

Workup

  1. customReaction
  2. customquenched with water
  3. extractionextracted with ethyl acetate, organic layer
  4. washwas washed with water and brine solution
  5. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-5b301298526f4a8088e363d6dca136bc
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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