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

HRID 1684692

반응식

HRID 1684692 반응식
[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.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.[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

참가 물질

7

반응물 3

HCID 78341,2-EpoxybutaneHCID 656671Sodium PyrosulfiteHCID 105671973-phenyl-2(S)-phthalimidopropionyl chloride

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

The solution containing the 3-phenyl-2(S)-phthalimidopropionyl chloride is diluted with 500 ml of toluene and treated with 72.11 g of 1,2-butylene oxide. 23.5 g of palladium-on-charcoal (5%) and 100 ml of toluene are added to the solution. The suspension is hydrogenated for 17 hours while stirring and then filtered, and the residue is washed with 200 ml of toluene. The filtrate and washings are combined and treated while stirring with a solution of 0.5 mol of sodium pyrosulfite in water. The phases are separated after 4.5 hours. The aqueous phase is washed with toluene. The toluene phases are washed with water. The combined aqueous phases are treated with toluene and 3N sulphuric acid and stirred at 60°. Thereafter, the phases are separated and the aqueous phase is extracted with toluene. The toluene phases are washed with water, combined, dried and evaporated. 3-Phenyl-2(S)-phthalimido-propan-1-al is obtained as a white solid, melting point 115°-117°, [a]D20 -200° (1% in ethyl acetate).

후처리

  1. filtrationfiltered
  2. washthe residue is washed with 200 ml of toluene
  3. additiontreated
  4. customThe phases are separated after 4.5 hours
  5. washThe aqueous phase is washed with toluene
  6. washThe toluene phases are washed with water
  7. additionThe combined aqueous phases are treated with toluene and 3N sulphuric acid
  8. stirringstirred at 60°
  9. customThereafter, the phases are separated
  10. extractionthe aqueous phase is extracted with toluene
  11. washThe toluene phases are washed with water
  12. customdried
  13. customevaporated

출처 및 근거

ORD 기록
ord-9458e356afa94165ab9bff536f200665
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05641886

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