Tributylphosphine → trans-4-[N-ethyl-N-(2-nitrobenzenesulfonyl)amino]-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide
反応式
O[C@H:2]1[CH2:7][C@@H:6]([CH3:8])[S:5](=[O:10])(=[O:9])[C:4]2[S:11][CH:12]=[CH:13][C:3]1=2.C(P(CCCC)CCCC)CCC.[CH2:27]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])(=[O:32])=[O:31])[CH3:28]>>[CH2:27]([N:29]([C@H:2]1[CH2:7][C@H:6]([CH3:8])[S:5](=[O:10])(=[O:9])[C:4]2[S:11][CH:12]=[CH:13][C:3]1=2)[S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])(=[O:31])=[O:32])[CH3:28]参加物
4
反応条件
- 温度
- -30 °C
実験手順
cis-4-hydroxy-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide (5 g), tributylphosphine (6.6 mL) and N-ethyl-2-nitrobenzenesulfonamide (6.17 g) are mixed under nitrogen atmosphere. It is cooled at −20/−30° C. Diisopropyl azadicarboxylate (4.8 mL) is added, maintaining the temperature. It is maintained under stirring, maintaining the temperature, for 4 hours. Tributylphosphine (1.5 mL) and diisopropyl azadicarboxylate (1.5 mL) are added. It is left to reach 20-25° C. and maintained for 30 minutes. It is cooled at 0-5° C.; it is filtered, washed with cold toluene and dried. After purifying by resuspension in methanol, 2.01 g of trans-4-[N-ethyl-N-(2-nitrobenzenesulfonyl)amino]-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide are obtained.