Trimethylsilyl iodide → HCID 19700501, compound
Reaction equation
I[Si](C)(C)C.[CH:6]1([C:12]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][C:18]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][P:32]([O:37]CC)([O:34]CC)=[O:33])=[CH:27][CH:26]=4)=[O:23])=[CH:19]3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>C(Cl)(Cl)(Cl)Cl>[CH:6]1([C:12]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][C:18]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][P:32]([OH:37])([OH:34])=[O:33])=[CH:27][CH:26]=4)=[O:23])=[CH:19]3)=[CH:14][CH:13]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Iodotrimethylsilane [(CH3)3SiI] (0.458 g) was added to a suspension of 7-cyclohexyl-N-(4-diethoxyphosphorylmethylphenyl)-3,4-dihydronaphthalene-2-carboxamide (0.5 g) in carbon tetrachloride (10 ml) at 0° C. After stirring at 0° C. for 1 hour and then at room temperature for 15 hours, this mixture was concentrated under reduced pressure. To the residue, methanol (6 ml) was added; this mixture was acidified with 1N HCl and stirred at room temperature for 30 minutes. The resulting crystals were collected by filtration and recrystallized from methanol-water to yield 7-cyclohexyl-N-(4-phosphonomethylphenyl)-3,4-dihydronaphthalene-2-carboxamide (0.28 g, 63%) as pale yellow prisms having a melting point of 203°-205° C.