Methyl morpholine oxide → [4-(4-Chlorophenoxy)-2-propylphenyl][4-chloro-2-fluoro-5-methoxyphenyl]methanone

HRID 1172826노트

반응식

HRID 1172826 반응식
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[CH:14][C:13]=2[CH2:26][CH2:27][CH3:28])[OH:11])=[C:4]([F:29])[C:3]=1[Si](C)(C)C.C[N+]1([O-])CCOCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.C(OCC)C.C1COCC1.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:15]2[CH:16]=[CH:17][C:12]([C:10]([C:5]3[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[CH:3][C:4]=3[F:29])=[O:11])=[C:13]([CH2:26][CH2:27][CH3:28])[CH:14]=2)=[CH:24][CH:23]=1

참가 물질

9

반응물 3

HCID 82029Methyl morpholine oxideHCID 2724141Tetrabutylammonium FluorideHCID 86622409[4-Chloro-2-fluoro-5-methoxy-3-(trimethylsilyl)phenyl][4-(4-chlorophenoxy)-2-propylphenyl]methanol

생성물 1

HCID 68689947[4-(4-Chlorophenoxy)-2-propylphenyl][4-chloro-2-fluoro-5-methoxyphenyl]methanone

시약·촉매·용매 5

HCID 178419074HCID 178419074, 화합물촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

A mixture of the product from Step 2 (1.9 g, 3.7 mmol), N-methylmorpholine-N-oxide (0.70 g, 6.0 mmol), tetrapropylammonium perruthenate (70 mg, 0.2 mmol) and 4 Å molecular sieves (2.0 g) in dichloromethane (20 mL) was stirred at 25° C. for 1 h. The reaction mixture was diluted with diethyl ether (60 mL) and filtered through a short path of silica gel. Removal of the solvent gave the crude product. The crude product was dissolved in THF (20 mL) and treated with tetrabutylammonium fluoride (1M in THF, 5.6 mL, 5.6 mmol) for 10 min. The reaction mixture was diluted with ethyl acetate, washed with brine, dried and concentrated. The residue was purified by chromatography on silica gel to give the title product.

후처리

  1. filtrationfiltered through a short path of silica gel
  2. customRemoval of the solvent
  3. customgave the crude product
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-b99a6ec23c2e45b0893015d613d683f8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834036B2

반응 노트

불러오는 중…