Triphenylphosphine → HCID 59201006, compound

HRID 1690151Notes

Reaction equation

HRID 1690151 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:18]=[C:19]([CH:23](O)[CH3:24])[CH:20]=[CH:21][CH:22]=2)=[C:14]([CH2:28][CH2:29][CH3:30])[CH:13]=1)([O:8]COC)[C:4]([F:7])([F:6])[F:5].[CH3:33][CH:34]([O:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2([CH3:50])[NH:47][C:46](=[O:48])[NH:45][C:44]2=[O:49])=[CH:39][CH:38]=1)[CH3:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCOC(/N=N/C(OCC)=O)=O>[F:32][C:2]([F:31])([F:1])[C:3]([C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:18]=[C:19]([CH:23]([N:45]3[C:44](=[O:49])[C:43]([C:40]4[CH:41]=[CH:42][C:37]([O:36][CH:34]([CH3:33])[CH3:35])=[CH:38][CH:39]=4)([CH3:50])[NH:47][C:46]3=[O:48])[CH3:24])[CH:20]=[CH:21][CH:22]=2)=[C:14]([CH2:28][CH2:29][CH3:30])[CH:13]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 30521535-methyl-5-[4-(propan-2-yloxy)phenyl]imidazolidine-2,4-dioneHCID 59200893HCID 59200893, compound

Product 1

HCID 59201006HCID 59201006, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 5462977Diethyl azodicarboxylateSolvent

Procedure

To a solution of 1-(3-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)phenyl) ethanol (40.0 mg, 85.8 mmol), 5-(4-(1-methylethoxy)phenyl)-5-methylimidazolidine-2,4-dione (32.0 mg) and triphenylphosphine (56.3 mg) in tetrahydrofuran (5 mL), diethylazodicarboxylate (about 2.2 mol/L toluene solution, 97.5 μL) was added under ice-cold conditions. After completion of the reaction, the reaction solution was concentrated in vacuo. The obtained residue was purified using silica-gel thin-layer chromatography (hexane/ethyl acetate). The obtained compound was added with 2 mol/L hydrogen chloride-ethyl acetate solution (1 mL) at room temperature. After completion of the reaction, the solution was concentrated in vacuo and purified using thin-layer silica-gel column chromatography (hexane/ethyl acetate) and the title compound (37.2 mg, yield 66%) was obtained as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated in vacuo
  3. customThe obtained residue was purified
  4. additionThe obtained compound was added with 2 mol/L hydrogen chloride-ethyl acetate solution (1 mL) at room temperature
  5. customAfter completion of the reaction
  6. concentrationthe solution was concentrated in vacuo
  7. custompurified

Sources & evidence

ORD record
ord-a1e0785b81da402d8d41535baae977c1
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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