Chloromethyl(1,1-dimethylethoxy)methyl(phenyl)silane → (1,1-dimethylethoxy)methyl(phenyl)(1H-1,2,4-triazol-1-ylmethyl)silane
Reaction equation
Cl[CH2:2][Si:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Na].[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1>CN(C)C=O>[CH3:13][C:12]([CH3:15])([O:11][Si:3]([CH3:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:2][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[CH3:14]Participants
Procedure
A mixture of 3.6 g (0.015 mol) of chloromethyl(1,1-dimethylethoxy)methyl(phenyl)silane and 1.3 g (0.015 mol) of 1,2,4-triazole sodium salt in 8 ml of dimethylformamide was stirred at 80° for 2 hours, cooled, and poured onto water. The resulting mixture was extracted with ether, and the ether extracts were washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.7 g of a yellow oil. Chromatography on silica gel, eluting with 50:50 ethyl acetate-hexanes, provided 1.5 g (36%) of the title compound as a pale yellow oil: nD21 1.5134; ir (neat) 3120, 3070, 3045, 2975, 2925, 1500, 1425, 1380, 1365, 1270, 1255, 1240, 1190, 1140, 1115, 1050, 1020, 1010, 830, 810, 790, 740, 700, 680 cm-1 ; nmr (CDCl3): 0.6 (3H, s), 1.3 (9H, s), 3.9 (2H, s), 7.3-7.7 (5H, m), 7.9 (1H, s) and 8.0 (1 H, s).
Workup
- temperaturecooled
- additionpoured onto water
- extractionThe resulting mixture was extracted with ether
- washthe ether extracts were washed with water and brine
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-81747da57cb341cda3887f53c0944022
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04510136
Reaction notes
Loading…