Triphenylphosphine → HCID 10737216, compound

HRID 2294803Notes

Reaction equation

HRID 2294803 reaction equation
C([O:4][C:5]([C:7]1[CH:8]=[C:9]([S:13]([N:16]2[C:20](=[O:21])[CH2:19][N:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17]2=[O:28])(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1)=[O:6])C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)=O.O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:5]([C:7]1[CH:8]=[C:9]([S:13]([N:16]2[C:20](=[O:21])[CH2:19][N:18]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:17]2=[O:28])(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1)([OH:6])=[O:4]

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 11795253HCID 11795253, compound

Product 1

HCID 10737216HCID 10737216, compoundYield 97.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of a 10% solution of formic acid in tetrahydrofuran (THF), were dissolved 400 mg (1.00 mmol) of 3-(3-allyloxycarbonylbenzenesulfonyl)-1-phenyl-imidazolidin-2,4-dione obtained in Example 33. The resultant solution wad deaerated under reduced pressure. To the solution, 50 mg of tetrakis(triphenylphosphine)palladium and 50 mg of triphenylphosphine were added, followed by stirring at room temperature for 2 hours under shielding from the light. After completion of the reaction, the liquid reaction mixture was concentrated under reduced pressure, and crude crystals obtained as residue were collected by filtration, washed with ethyl acetate and then dried, thereby obtaining 350 mg (yield: 97.0%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customthe liquid reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customcrude crystals obtained as residue
  5. filtrationwere collected by filtration
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-00a2fc6b985843e08b192add7dd284e8
Source dataset
uspto-grants-1997_11
Patent number
US05691335

Reaction notes

Loading…