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

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

反応物 4

HCID 8028Tetrahydrofuran2 回

HCID 142176Phenyl triflimide

HCID 2733832Lithium hexamethyldisilazane

HCID 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.