Triphenylphosphine → HCID 22107146, compound

HRID 1456620Notes

Reaction equation

HRID 1456620 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.[OH:38][C:39]1[CH:51]=[CH:50][C:42]2OC3C=CC=CC=3[C:41]=2[CH:40]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH:15]1[C:16]2[C:40]3[CH:41]=[CH:42][CH:50]=[CH:51][C:39]=3[O:38][C:17]=2[CH:18]=[CH:2][C:3]=1[O:4][CH:5]1[CH2:6][CH:7]([C:9]([O:11][CH3:19])=[O:10])[NH:8][C:12]1=[O:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 665872-DibenzofuranolHCID 5462977Diethyl azodicarboxylateHCID 54262066HCID 54262066, compound

Product 1

HCID 22107146HCID 22107146, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2 °C

Procedure

A mixture of the compound prepared as described in Example 4 (0.800 g), triphenylphosphine (1.450 g), and 2-hydroxydibenzofuran(1.019 g) intetrahydrofuran (7.0 ml) was cooled to approximately 2° C., and treated with a solution of diethylazodicarboxylate (0.963 g) in tetrahydrofuran (2.0 ml) over a two minute period. After the addition was complete, the reaction was allowed to warm to room temperature. After about 15.5 hours, the solution was concentrated in vacuo. The residue was diluted with toluene (5 ml), the insoluble material removed by filtration, and the filtrate concentrated is vacuo. The oil was dissolved in ethyl acetate and purified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min), eluting with ethyl acetate/hexane (1:1) until first band elutes then solvent switched to hexane:ethyl acetate (1:3). The fractions containing the title compound were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to give methyl 3-(2-dibenzofuranoxy)-2-pyrrolidone-5-carboxylate (427 mg). This material contains triphenylphosphine oxide as an impurity.

Workup

  1. additionA mixture of the compound
  2. customprepared
  3. additionAfter the addition
  4. temperatureto warm to room temperature
  5. concentrationthe solution was concentrated in vacuo
  6. additionThe residue was diluted with toluene (5 ml)
  7. customthe insoluble material removed by filtration
  8. concentrationthe filtrate concentrated
  9. dissolutionThe oil was dissolved in ethyl acetate
  10. custompurified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min)
  11. washeluting with ethyl acetate/hexane (1:1) until first band elutes
  12. additionThe fractions containing the title compound
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aad81ee00837427196e69ec9b88ddcdf
Source dataset
uspto-grants-1998_12
Patent number
US05843997

Reaction notes

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