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

HRID 279353

反応式

HRID 279353 の反応式
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]

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 142176Phenyl triflimideHCID 2733832Lithium HexamethyldisilazideHCID 15541825HCID 15541825、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fb7757cd6818401497f915bffbb7bdfa
出典データセット
uspto-grants-2002_03
特許番号
US06362230B1

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