Triphenylphosphine → HCID 10093715, compound

HRID 1073531Notes

Reaction equation

HRID 1073531 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[C:14]1([N:20]2[CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:23](=[O:31])[NH:22][C:21]2=[O:32])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:32]=[C:21]1[N:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:23](=[O:31])[N:22]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 292983Nonanoic acid, 9-hydroxy-, methyl esterHCID 11658881HCID 11658881, compound

Product 1

HCID 10093715HCID 10093715, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl axodicarboxylate (1.39 g, 8 mmol) in THF (5 mL, was added dropwise to a stirred solution of methyl 9-hydroxynonanoate (1.50 g, 8 mmol), 3,4-diphenylimidazolidine-2,5-dione (2.02 g, 8 mmol) obtained according to the procedure of K. C. Joshi, et al., J. Het. Chem., 18, 1651-1653 (1981) and triphenylphosphine (2.10 g, 8 mmol) in THF (35 mL). The mixture was stirred at room temperature for 72 hours, the THF removed in vacuo and the residue triturated with a mixture of hexanes and diethyl ether. The mixture was filtered, the filtrate concentrated and subjected to chromatography on a column of silica gel using a mixture of hexanes and ethyl acetate (3:2) as eluent. Elution gave methyl 2,5-dioxo-3,4-diphenyl-1-imidazolidinenonanoate (2.78 g, 82%), mp 69°-72° C.

Workup

  1. customobtained
  2. customthe THF removed in vacuo
  3. customthe residue triturated with a mixture of hexanes and diethyl ether
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated
  6. additiona mixture of hexanes and ethyl acetate (3:2) as eluent
  7. washElution

Sources & evidence

ORD record
ord-9098a95daa7f48cbab6b53e229ab36a0
Source dataset
uspto-grants-1990_11
Patent number
US04970225

Reaction notes

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