Diphenylphosphine → HCID 19594736, compound

HRID 612595Notes

Reaction equation

HRID 612595 reaction equation
C([Li])CCC.C1(PC2C=CC=CC=2)C=CC=CC=1.C[O:20][C:21]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:22]=1[C:23]1[CH:24]=[CH:25][C:26]([O:35][CH2:36][CH2:37][CH3:38])=[CH:27][C:28]=1[C:29]2=[O:34]>C1COCC1>[OH:20][C:21]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:22]=1[C:23]1[CH:24]=[CH:25][C:26]([O:35][CH2:36][CH2:37][CH3:38])=[CH:27][C:28]=1[C:29]2=[O:34]

Participants

5

Reactant 3

HCID 70017Diphenylphosphine2×HCID 19594877HCID 19594877, compoundHCID 178418339Butyllithium

Product 1

HCID 19594736HCID 19594736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add n-butyl-lithium (4.80 mL, 0.012 mole) in THF (60 mL) dropwise to diphenylphosphine (Ph2PH, 2.34 g, 0.012 mole) at -20° C. Warm to resulting red solution to abient temperature, then stir for 30 minutes. Prepare a solution of 5-methoxy-2-propoxy-fluoren-9-one (0.88 g, 3.3 mmole) in THF (20 mL) and add to the stirred dark-red Ph2PH solution, stirring for an additional hour while the color changes from dark-red to brown, then heating at reflux for 15 minutes. Cool to abient temperature, then quench with a saturated solution of NH4Cl. Separate the THF layer, wash with brine, dry over MgSO4, filter and concentrate the filtrate to an orange oil. Dissolve the oil in CH2Cl2 and extract with 5% aq. NaOH (50 mL) as a purple solid formed in the aqueous layer.

Workup

  1. temperatureWarm
  2. customto resulting red solution
  3. stirringstirring for an additional hour while the color changes from dark-red to brown,
  4. temperaturethen heating
  5. temperatureat reflux for 15 minutes
  6. temperatureCool
  7. customquench with a saturated solution of NH4Cl
  8. customSeparate the THF layer
  9. washwash with brine
  10. dry with materialdry over MgSO4
  11. filtrationfilter
  12. concentrationconcentrate the filtrate to an orange oil
  13. dissolutionDissolve the oil in CH2Cl2
  14. extractionextract with 5% aq. NaOH (50 mL) as a purple solid
  15. customformed in the aqueous layer

Sources & evidence

ORD record
ord-44f6d6cc51a34557b21de11f7756c253
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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