Cyclohexene → Tetraethyl aminomethylenediphosphonate

HRID 1950737Notes

Reaction equation

HRID 1950737 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]([P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])[P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])C1C=CC=CC=1.C1CCCCC=1>CCO.[Pd]>[NH2:8][CH:9]([P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])[P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 10961905HCID 10961905, compound

Product 1

HCID 2773808Tetraethyl aminomethylenediphosphonateYield 119.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 1 (2.00 g, 4.14 mmol) was dissolved in EtOH (40 mL). To this solution was added palladium on carbon (10%, 1.5 g) and cyclohexene (2.5 mL, 24.7 mmol). The reaction mixture was refluxed under argon for 15 hours, filtered through celite and evaporated to give 2 as a slightly impure pale yellow oil (1.50 g, 119%), which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 1.35 (t, J=7.0, 12H), 3.58 (t, J=20.3, 1H), 3.65-3.90 (br s, 2H), 4.20-4.28 (m, 8H).

Workup

  1. temperatureThe reaction mixture was refluxed under argon for 15 hours
  2. filtrationfiltered through celite
  3. customevaporated

Sources & evidence

ORD record
ord-180de7e59d57417bb61d3038a3b7b248
Source dataset
uspto-grants-2013_03
Patent number
US08404664B2

Reaction notes

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