Triphenylphosphine → HCID 59235122, compound

HRID 1919761Notes

Reaction equation

HRID 1919761 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.[Si:48]([O:65][CH:66](O)[C:67]#[C:68][CH3:69])([C:61]([CH3:64])([CH3:63])[CH3:62])([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C1(C)C=CC=CC=1.O1CCCC1>[Si:48]([O:65][CH2:66][C:67]#[C:68][CH2:69][N:4]1[C:3](=[O:8])[C:2]([CH3:1])([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]1=[O:7])([C:61]([CH3:62])([CH3:63])[CH3:64])([C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 30521535-methyl-5-[4-(propan-2-yloxy)phenyl]imidazolidine-2,4-dioneHCID 66720523HCID 66720523, compoundHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 59235122HCID 59235122, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-5-[4-(1-methylethoxy)phenyl]imidazolidine-2,4-dione (248 mg), triphenylphosphine (655 mg) and a solution of ethyl azodicarboxylate in toluene (2.2 mol/L, 1.00 mL) were added to a mixed solution of t-butyl-diphenylsilyloxy-2-butyn-1-ol (326 mg, 1.00 mmol) in tetrahydrofuran (10 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 303 mg of the title compound (yield: 55%) 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-c74219f3f3664197adc72b7a5d0c471f
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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