Diethyl vinylphosphonate → {2-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-ethyl}-phosphonic acid diethyl ester

HRID 920591Notes

Reaction equation

HRID 920591 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:22]([P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])=[CH2:23]>CC#N>[CH2:26]([O:25][P:24]([CH2:22][CH2:23][N:18]1[CH2:19][CH2:20][O:21][CH:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)[CH2:17]1)(=[O:31])[O:28][CH2:29][CH3:30])[CH3:27]

Participants

4

Reactant 2

HCID 69629Diethyl vinylphosphonateHCID 670323512-(4-Octyloxy-phenyl)-morpholine

Product 1

HCID 86670016{2-[2-(4-Octyloxy-phenyl)-morpholin-4-yl]-ethyl}-phosphonic acid diethyl esterYield 31.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(4-octyloxy-phenyl)-morpholine (0.83 g; 2.9 mmol) and diethyl vinylphosphonate (0.53 ml; 3.4 mmol) in CH3CN (10 mL) was heated under reflux for 3 days. After cooling to RT the mixture was concentrated in vacuo and the residue was purified by column chromatography (SiO2, EtOAc: MeOH 90:10) to afford {2-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-ethyl}-phosphonic acid diethyl ester (0.42 g)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. concentrationwas concentrated in vacuo
  4. customthe residue was purified by column chromatography (SiO2, EtOAc: MeOH 90:10)

Sources & evidence

ORD record
ord-b58f3d8f19504ed68a87765bd9fa0773
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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