Tetrahydrofuran → N-[2-[4-[4-formylphenyl]-3-cyclohexen-1-yl]-propyl] 2-propanesulfonamide

HRID 279353

반응식

HRID 279353 반응식
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][CH:10]([CH:13]([CH3:22])[CH2:14][NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[CH2:9][CH:8]=1)(=O)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:35]1[CH:40]=[CH:39][C:38](N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=[CH:37][CH:36]=1.C1C[O:59][CH2:58]C1>>[CH:58]([C:38]1[CH:39]=[CH:40][C:35]([C:7]2[CH2:12][CH2:11][CH:10]([CH:13]([CH3:22])[CH2:14][NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[CH2:9][CH:8]=2)=[CH:36][CH:37]=1)=[O:59]

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 142176Phenyl triflimideHCID 2733832Lithium HexamethyldisilazideHCID 15541825HCID 15541825, 화합물

생성물 1

HCID 9841299N-[2-[4-[4-formylphenyl]-3-cyclohexen-1-yl]-propyl] 2-propanesulfonamide수율 26%

실험 절차

N-[2-[4-[[(trifluoromethyl)sulfonyl]oxy]-3-cyclohexen-1-yl]propyl] 2-propanesulfonamide: To a −78° C. solution of 1.0 g (3.82 mmol) of the material prepared in Preparation 2 in 6 ml of THF was added 8.4 ml of a 1 M solution of lithium bis(trimethylsilyl)amide in THF (8.4 mmol). The bath was removed and the mixture was stirred for 30 min and then 1.46 g (4.09 mmol) of N-phenyltrifluoromethane sulfonimide was added at ambient temperature. The mixture was stirred for 24 h. The reaction was quenched with NH4Cl saturated solution and extracted three times with ethyl acetate. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (125 g of silica gel, 15% ethyl acetate/hexane) of the residue afforded 395 mg (26%) of the title compound.

후처리

  1. customThe bath was removed
  2. stirringThe mixture was stirred for 24 h
  3. customThe reaction was quenched with NH4Cl saturated solution
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fb7757cd6818401497f915bffbb7bdfa
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362230B1

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