Acetic Acid → Racemic 6-chloro-3-(3,3-dimethyl-1-nitromethyl-butyl)-1,3-dihydro-indol-2-one

HRID 2065391노트

반응식

HRID 2065391 반응식
[N+:1]([CH3:4])([O-:3])=[O:2].C[O-].[Na+].[Cl:8][C:9]1[CH:17]=[C:16]2[C:12](/[C:13](=[CH:19]/[CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])/[C:14](=[O:18])[NH:15]2)=[CH:11][CH:10]=1.C(O)(=O)C>CO>[Cl:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]([CH:19]([CH2:4][N+:1]([O-:3])=[O:2])[CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:14](=[O:18])[NH:15]2)=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 10942334Sodium MethoxideHCID 86615083Z-6-chloro-3-(3,3-dimethyl-butylidene)-1,3-dihydro-indol-2-one

생성물 1

HCID 58398993Racemic 6-chloro-3-(3,3-dimethyl-1-nitromethyl-butyl)-1,3-dihydro-indol-2-one수율 90%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of nitromethane (Aldrich) (1.7 g, 27 mmol) in methanol (20 mL) was slowly added a methanolic solution (Aldrich, 25 wt. %) of sodium methoxide (5.9 g, 27 mmol). After the mixture was stirred at room temperature for 10 min, a solution of E/Z-6-chloro-3-(3,3-dimethyl-butylidene)-1,3-dihydro-indol-2-one (3.4 g, 14 mmol) in methanol (20 mL) was added. The reaction mixture was stirred at room temperature for 2 h, then acetic acid (2.5 g, 41 mmol) was added. The mixture was concentrated to a small volume, then the residue was partitioned between ethyl acetate and water. The organic layer was separated, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:5, 1:3) to give the racemic 6-chloro-3-(3,3-dimethyl-1-nitromethyl-butyl)-1,3-dihydro-indol-2-one as a white foam (3.8 g, 90%).

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 2 h
  2. concentrationThe mixture was concentrated to a small volume
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated aqueous NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography (EtOAc:hexanes=1:5, 1:3)

출처 및 근거

ORD 기록
ord-372a312fd5724a9f9fbcfe4cf12ea632
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288431B2

반응 노트

불러오는 중…