Triphenylphosphine → HCID 67767166, compound

HRID 1900622Notes

Reaction equation

HRID 1900622 reaction equation
C[C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH:5]([C:12]([OH:14])=O)[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8].[C:19]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:38]([C:41]1[CH:42]=[C:43](C2C=CC(O)=CC=2)[CH:44]=[CH:45][CH:46]=1)[CH2:39][CH3:40].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:41]1([CH2:38][CH2:39][CH2:40][C:17]2[CH:18]=[CH:2][C:3]([O:4][CH:5]3[CH2:6][CH:7]([C:9]([O:11][CH3:19])=[O:10])[NH:8][C:12]3=[O:14])=[CH:15][CH:16]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22107093HCID 22107093, compoundHCID 54262066HCID 54262066, compound

Product 1

HCID 67767166HCID 67767166, compoundYield 122.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound prepared as described in Example 4 (0.5349 g), triphenylphosphine (1.00 g), and 4-(3-propylphenyl) phenol (0.8100 g) in tetrahydrofuran (4.7 ml) was cooled to approximately 1°-2° C., and treated with a solution of diethylazodicarboxylate (0.6645 g) over a two minute period. After the addition was complete, the reaction suspension was allowed to warm to room temperature. After about 28.5 hours, the resulting brown solution was concentrated in vacuo. The residue was diluted with chloroform (2 ml), the insoluble material removed by filtration, and the filtrate concentrated in vacuo to an oil. The oil was dissolved in methylene chloride and purified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min), eluting with 50% ethyl acetate/hexane until the first band elutes then solvent switched to 100% ethyl acetate. The fractions containing the desired compound were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to give 0.916 g of methyl 3-(4-(3-phenylpropyl)phenoxy]-2-pyrrolidone-5-carboxylate as a white solid.

Workup

  1. additionA mixture of the compound
  2. customprepared
  3. temperaturewas cooled to approximately 1°-2° C.
  4. additionAfter the addition
  5. concentrationthe resulting brown solution was concentrated in vacuo
  6. additionThe residue was diluted with chloroform (2 ml)
  7. customthe insoluble material removed by filtration
  8. concentrationthe filtrate concentrated in vacuo to an oil
  9. dissolutionThe oil was dissolved in methylene chloride
  10. custompurified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min)
  11. washeluting with 50% ethyl acetate/hexane until the first band elutes
  12. additionThe fractions containing the desired compound
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20bbd759c73a467381ff94feff642f3c
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

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