Pyridine → 5,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(4-methoxyphenyl)-2-(5H)-furanone

HRID 325178

반응식

HRID 325178 반응식
[OH:1][C:2]([CH3:16])([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.N1C=CC=CC=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](Cl)=[O:33])=[CH:27][CH:26]=1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.CCOC(C)=O.Cl>[CH3:15][C:2]1([CH3:16])[O:1][C:32](=[O:33])[C:31]([C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[C:3]1[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1

참가 물질

8

반응물 4

HCID 1049PyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27346884-Methoxyphenylacetyl chlorideHCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

생성물 1

HCID 155167095,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(4-methoxyphenyl)-2-(5H)-furanone

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a cold solution (0° C.) of 2-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-propane-1-one (726 mg, 3.5 mmol, Step 3), pyridine (0.5 mL, 6.2 mmol) in CH2Cl2 (10 mL) was added 4-methoxyphenylacetyl chloride (1.5 g, 8.4 mmol) over 2 minutes. The resulting yellow solution was stirred at r.t. for 18 h. Then DBU was added in portions every 30 min. (3×1.0 mL, 3×6.7 mmol). The reaction was diluted with EtOAc (100 mL) and 1N HCl (50 mL). The organic layer was washed with water (50 mL), dried over MgSO4 and concentrated. The crude product was purified first by flash chromatography eluted with 40% EtOAc in hexane and then by crystallization in EtOAc and hexane (1:1, 26 mL) to give the title compound as a white solid.

후처리

  1. washThe organic layer was washed with water (50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified first by flash chromatography
  5. washeluted with 40% EtOAc in hexane
  6. customby crystallization in EtOAc

출처 및 근거

ORD 기록
ord-8ff12c79c6c343788b1af6fba6af283c
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06222048B1

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