(4-Cyanobutyl)(triphenyl)phosphanium bromide → HCID 67746033, compound

HRID 374827Notes

Reaction equation

HRID 374827 reaction equation
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].CC(C)([O-])C.[K+].C(NC1C=C([C:43]2[C:48]([C:49]([C:51]3[C:52]([C:57]4C=CC=[C:59]([NH:63][C:64](=[O:66])[CH3:65])[CH:58]=4)=NC=C[CH:56]=3)=O)=[CH:47][CH:46]=[CH:45][N:44]=2)C=CC=1)(=O)C>O1CCCC1>[C:64]([NH:63][C:59]1[CH:56]=[C:51](/[C:49](/[C:48]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)=[CH:7]\[CH2:6][CH2:5][CH2:4][C:2]#[N:3])[CH:52]=[CH:57][CH:58]=1)(=[O:66])[CH3:65]

Participants

5

Reactant 3

HCID 11418829(4-Cyanobutyl)(triphenyl)phosphanium bromideHCID 23665647Potassium tert-butoxideHCID 53837382HCID 53837382, compound

Product 1

HCID 67746033HCID 67746033, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 25.5 g of 4-cyanobutyl-triphenylphosphonium bromide and 14 g of potassium tert.butoxide in 200 ml of tetrahydrofuran are added, at -40° C., 12 g of 3-acetylaminophenyl-3-pyridylketone. The mixture is stirred for 3 hours at ambient temperature and the reaction mixture is decomposed by the addition of 50 ml of ice water. The mixture is concentrated by evaporation, the residue is taken up in water and extracted with ethyl acetate. The organic phase is evaporated down and the residue is purified over a silica gel column with dichloromethane/ethanol=40:1. The product fraction is evaporated down and the residue is recrystallised from ethyl acetate/diisopropylether.

Workup

  1. additionare added, at -40° C.
  2. concentrationThe mixture is concentrated by evaporation
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is evaporated down
  5. customthe residue is purified over a silica gel column with dichloromethane/ethanol=40:1
  6. customThe product fraction is evaporated down
  7. customthe residue is recrystallised from ethyl acetate/diisopropylether

Sources & evidence

ORD record
ord-badf36baa0474f23911c7e464c69e79f
Source dataset
uspto-grants-1996_01
Patent number
US05482948

Reaction notes

Loading…