Lawesson's reagent → Ethyl 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carboxylate
Reaction equation
[Si:1]([O:18][CH2:19][C:20]([NH:22][NH:23][C:24](=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>O1CCCC1>[Si:1]([O:18][CH2:19][C:20]1[S:40][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:23][N:22]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
To a solution of ethyl [2-({[tert-butyl(diphenyl)silyl]oxy}acetyl)hydrazino](oxo)acetate (3.20 g) in tetrahydrofuran (30 mL) was added Lawesson's reagent (3.02 g), and the mixture was stirred at room temperature for 24 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and the title compound (3.05 g, yield 96%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).