Potassium Carbonate → 1-(4-(4,4-Bis(diethylphosphono)butoxy)phenyl)prop-2-en-1-one

HRID 1950742Notes

Reaction equation

HRID 1950742 reaction equation
[CH3:1][CH2:2][O:3][P:4]([O:19][CH2:20][CH3:21])([CH:6]([P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH2:9]I)=[O:5].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:32])[CH:30]=[CH2:31])=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:2]([O:3][P:4]([CH:6]([P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH2:9][O:22][C:23]1[CH:24]=[CH:25][C:26]([C:29](=[O:32])[CH:30]=[CH2:31])=[CH:27][CH:28]=1)([O:19][CH2:20][CH3:21])=[O:5])[CH3:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 160369274-AcryloylphenolHCID 25138734HCID 25138734, compound

Product 1

HCID 251387351-(4-(4,4-Bis(diethylphosphono)butoxy)phenyl)prop-2-en-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of iodide 33 (3.1 g, 6.8 mmol), phenol 27 (1.21 g, 8.17 mmol) and K2CO3 (1.033 g, 7.47 mmol) in acetone (75 mL) was refluxed for 6.5 h. The mixture was cooled, filtered and evaporated. The residue was redissolved in CH2Cl2 (170 mL), filtered through Celite and evaporated to give crude 34 (3.2 g, 99%) which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 1.28-1.39 (m, 12H), 1.89-2.25 (m, 4H), 2.26-2.48 (m, 1H), 4.05 (t, J=5.7, 2H), 4.12-4.26 (m, 8H), 5.87 (dd, J=10.6, 1.8, 1H), 6.42 (dd, J=16.9, 1.8, 1H), 6.93 (d, J=8.8, 2H), 7.17 (dd, J=17.0, 10.4, 1H), 7.95 (d, J=8.8, 2H).

Workup

  1. temperaturewas refluxed for 6.5 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue was redissolved in CH2Cl2 (170 mL)
  6. filtrationfiltered through Celite
  7. customevaporated

Sources & evidence

ORD record
ord-8f609c8a95ed46ee8bdaa378161056b3
Source dataset
uspto-grants-2013_03
Patent number
US08404664B2

Reaction notes

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