1,2-Epoxybutane → 3-Phenyl-2(S)-phthalimidopropan-1-al

HRID 342909

Reaction equation

HRID 342909 reaction equation
[C:1]1([CH2:7][C@H:8]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1OC1CC>C1(C)C=CC=CC=1.[Pd]>[C:1]1([CH2:7][C@H:8]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH:9]=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 78341,2-EpoxybutaneHCID 105671973-phenyl-2(S)-phthalimidopropionyl chloride

Product 1

HCID 110658013-Phenyl-2(S)-phthalimidopropan-1-al

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

The solution containing the 3-phenyl-2(S)-phthal-imidoproionyl chloride was diluted with 500 ml of toluene and combined with 72.11 g of 1,2-butylene oxide. 23.5 g of palladium on carbon (5%) and 100 ml of toluene were added to the solution. The suspension was hydrogenated for 17 hours with stirring and then filtered and the residue washed with 200 ml of toluene, wherein 3-phenyl-2(S)-phthalimidopropan-1-al was obtained.

Workup

  1. filtrationfiltered
  2. washthe residue washed with 200 ml of toluene

Sources & evidence

ORD record
ord-773620b4408d4245bbc99e84e23a45f9
Source dataset
uspto-grants-1999_01
Patent number
US05859248

Linked notes

Loading…