Methanol → HCID 18618679, 화합물

HRID 1919236노트

반응식

HRID 1919236 반응식
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.CO.C[N+]1([O-])CCOCC1>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 82029Methyl morpholine oxideHCID 610239HCID 610239, 화합물

생성물 1

HCID 18618679HCID 18618679, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

The aromatic enone 46 (321 mg, 1.20 mmol) was dissolved in anhydrous THF (6 mL) and anhydrous MeOH (6 ml). Added 2 small scoops of Pd 10% on activated C, placed under an atmosphere of hydrogen and allowed to stir for 2 hours at room temperature. Purged with nitrogen, filtered through Celite and removed solvent by evaporation under vacuum. The benzylic alcohol is reoxidized to the ketone by the following procedure. The crude was taken back in anhydrous CH2Cl2 (10 mL), with 3 Å molecular sieves, TPAP (1 scoop) was added followed by NMO (212 mg, 1.8 mmol). Stirred at room temperature for 30 minutes and filtered through a plug of silica gel. Solvent was evaporated under vacuum and purified by column chromatography using 10% EtOAc/Hexane.

후처리

  1. customPurged with nitrogen
  2. filtrationfiltered through Celite
  3. customremoved solvent
  4. customby evaporation under vacuum
  5. additionwas added
  6. stirringStirred at room temperature for 30 minutes
  7. filtrationfiltered through a plug of silica gel
  8. customSolvent was evaporated under vacuum
  9. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-88d8d448171c476ca5c56d2592b2845b
출처 데이터셋
uspto-grants-2012_05
특허 번호
USRE043343E1

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