N,N,N',N'-Tetramethylethylenediamine → N-Phenyl-2-(dicyclohexylphosphino)indol

HRID 732878Notes

Reaction equation

HRID 732878 reaction equation
CN([CH2:4][CH2:5][N:6]([CH3:8])[CH3:7])C.[Li][CH2:10][CH2:11][CH2:12][CH3:13].Cl[P:15]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CCCCCC>[C:5]1([N:6]2[C:8]3[C:21](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:20]=[C:7]2[P:15]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:4]=1

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2734135ChlorodicyclohexylphosphineHCID 178418339Butyllithium

Product 1

HCID 53411821N-Phenyl-2-(dicyclohexylphosphino)indol

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Conditions

Temperature
75 °C

Procedure

1.6 ml (15 mmol.) of TMEDA are added to 1.93 g (10 mmol.) of 1 in 30 ml of hexane. A solution (1.6 M in hexane) of n-BuLi (6.25 ml, 10 mmol.) is added dropwise. After 3 hours, reflux (75° C.), the colour has deepened from yellow to orange. Without cooling, a solution of 2.2 ml (10 mmol.) of chlorodicyclohexylphosphane in 20 ml of hexane is added dropwise. Refluxing is carried out for a further one hour, the colour of the mixture lightening again and a white solid precipitating. After cooling, 30 ml of water are added to the mixture. The aqueous phase is extracted 3 times using 20 ml of hexane each time. The combined organic phases are washed with 10 ml of water, dried over Na2SO4 and concentrated in vacuo (45° C.). The yellow residue is boiled for 30 minutes in 30 ml of MeOH. After cooling to RT, the resulting product is filtered off (660 mg, 17%).

Workup

  1. temperatureWithout cooling
  2. temperatureRefluxing
  3. waitis carried out for a further one hour
  4. customthe colour of the mixture lightening again and a white solid precipitating
  5. temperatureAfter cooling
  6. addition30 ml of water are added to the mixture
  7. extractionThe aqueous phase is extracted 3 times
  8. washThe combined organic phases are washed with 10 ml of water
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo (45° C.)
  11. waitThe yellow residue is boiled for 30 minutes in 30 ml of MeOH
  12. temperatureAfter cooling to RT
  13. filtrationthe resulting product is filtered off (660 mg, 17%)

Sources & evidence

ORD record
ord-fee29dc704834d14a984a5d955705db5
Source dataset
uspto-grants-2009_09
Patent number
US07589081B2

Reaction notes

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