N,N,N',N'-Tetramethylethylenediamine → 2-[Bis(tricyclo[3.3.1.13,7]dec-1-yl)phosphino]-1-phenyl-1H-pyrrole

HRID 732876

Reaction equation

HRID 732876 reaction equation
CN(CCN(C)C)C.[C:9]1([N:15]2[CH:19]=[CH:18][CH:17]=[CH:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([Li])CCC.[C:25]12([P:35]([C:37]34[CH2:46][CH:41]5[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]5)[CH2:38]3)[CH2:44]4)Cl)[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2>CCCCCC.O>[C:9]1([N:15]2[CH:19]=[CH:18][CH:17]=[C:16]2[P:35]([C:37]23[CH2:38][CH:39]4[CH2:40][CH:41]([CH2:42][CH:43]([CH2:45]4)[CH2:44]2)[CH2:46]3)[C:25]23[CH2:26][CH:27]4[CH2:33][CH:31]([CH2:30][CH:29]([CH2:28]4)[CH2:34]2)[CH2:32]3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 124801-PhenylpyrroleHCID 11110495Di-1-adamantylchlorophosphineHCID 178418339Butyllithium

Product 1

HCID 121867732-[Bis(tricyclo[3.3.1.13,7]dec-1-yl)phosphino]-1-phenyl-1H-pyrrole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
60 °C

Procedure

1.6 ml of TMEDA (15 mmol.) are added to a suspension of 1.43 g (10 mmol.) of N-phenylpyrrole in 30 ml of hexane. 6.25 ml of 1.6 molar n-butyllithium solution (10 mmol.) are added at room temperature. The mixture is then heated for 2.5 hours at reflux temperature (solution 1). In another flask, 3.36 g (10 mmol.) of di-1-adamantylchlorophosphane are mixed with 40 ml of hexane and heated to 76° C. (solution 2). The boiling solution 1 is then slowly transferred into solution 2, which is at 76° C., by means of a cannula. The mixture is then boiled for a further 2 hours at reflux, the solution is cooled, and 20 ml of water are added thereto. The organic phase is filtered off over magnesium sulfate. The solution is concentrated in vacuo; 15 ml of toluene are added thereto, and the mixture is heated to 60° C. and then cooled. After one day at room temperature, the product is filtered off. Yield: 3.3 g (75%).

Workup

  1. temperatureThe mixture is then heated for 2.5 hours
  2. customis at 76° C., by means of a cannula
  3. temperatureat reflux
  4. temperaturethe solution is cooled
  5. filtrationThe organic phase is filtered off over magnesium sulfate
  6. concentrationThe solution is concentrated in vacuo
  7. addition15 ml of toluene are added
  8. temperaturecooled
  9. waitAfter one day at room temperature
  10. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-2e2e1e695dd84700a40876b63117ff6e
Source dataset
uspto-grants-2009_09
Patent number
US07589081B2

Linked notes

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