Triphenylphosphine → 3-[4-[4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylphenyloxy]-1-methylbutyl]-5-methyl-5-[4-(1-methylethoxy)phenyl]imidazolidine-2,4-dione

HRID 1919772Notes

Reaction equation

HRID 1919772 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O.[F:48][C:49]([F:76])([F:75])[C:50]([C:59]1[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH2:67][CH2:68][CH:69](O)[CH3:70])=[C:61]([CH2:72][CH2:73][CH3:74])[CH:60]=1)([O:55]COC)[C:51]([F:54])([F:53])[F:52]>C1(C)C=CC=CC=1.O1CCCC1>[F:48][C:49]([F:75])([F:76])[C:50]([C:59]1[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH2:67][CH2:68][CH:69]([N:4]2[C:3](=[O:8])[C:2]([CH3:1])([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=3)[NH:6][C:5]2=[O:7])[CH3:70])=[C:61]([CH2:72][CH2:73][CH3:74])[CH:60]=1)([OH:55])[C:51]([F:52])([F:54])[F:53]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 30521535-methyl-5-[4-(propan-2-yloxy)phenyl]imidazolidine-2,4-dioneHCID 592350345-[4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyloxy]pentan-2-olHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 592349053-[4-[4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylphenyloxy]-1-methylbutyl]-5-methyl-5-[4-(1-methylethoxy)phenyl]imidazolidine-2,4-dioneYield 89%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-5-[4-(1-methylethoxy)phenyl]imidazolidine-2,4-dione (25.8 mg), triphenylphosphine (22.8 mg) and a solution of ethyl azodicarboxylate in toluene (2.2 mol/L, 34.7 μL) were added to a mixed solution of 5-[4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyloxy]pentan-2-ol (15.0 mg, 34.7 μmol) in tetrahydrofuran (1 mL) at room temperature. After completion of the reaction, the solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 19.0 mg of the title compound (yield: 89%) as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-827e3bd647e44ff2bcb0654c64ae0727
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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