Triphenylphosphine → HCID 59407956, compound

HRID 1093444Notes

Reaction equation

HRID 1093444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:32]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:32][CH2:11][CH2:10][CH2:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 57472866HCID 57472866, compound

Product 1

HCID 59407956HCID 59407956, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 66-2 (1.73 g) was dissolved in methylene chloride (20 ml), triphenylphosphine (2.43 g) and N-chlorosuccinimide (1.24 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and at room temperature for 2.5 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (50 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (1.76 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. washThe reaction mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionDiethyl ether (50 ml) was added
  7. filtrationthe precipitated triphenylphosphine oxide was filtered off
  8. concentrationThe concentrate of the filtrate
  9. customwas purified by silica gel column chromatography (hexane alone)

Sources & evidence

ORD record
ord-2329ed98834747a684997dae9dc528f5
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

Loading…