Imidazole → Tert-butyl-[[5-(methoxymethoxy)-2-methyl-phenyl]methoxy]-dimethyl-silane
Reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:13])=[C:9]([CH2:11][OH:12])[CH:10]=1.N1C=CN=C1.Cl[Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>ClCCl>[C:23]([Si:20]([O:12][CH2:11][C:9]1[CH:10]=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:6]=[CH:7][C:8]=1[CH3:13])([CH3:22])[CH3:21])([CH3:26])([CH3:25])[CH3:24]Participants
Procedure
[5-(methoxymethoxy)-2-methyl-phenyl]methanol (Intermediate 173, 1.9 g, 10 mmol) was dissolved in dichloromethane (10 ml) to give a colourless solution. 1H-imidazole (1.137 g, 16.7 mmol) and chloro(1,1-dimethylethyl)dimethylsilane (2.095 g, 13.9 mmol) were added. The reaction mixture immediately became a white suspension and was stirred at room temperature for 30 minutes. The reaction mixture was quenched with 10 ml of water and diluted with 10 ml of dichloromethane. Two phases were separated through a separating funnel. The organic phase was dried over Na2SO4 and evaporated under vacuum and the residue was purified by flash chromatography (Biotage system) on silica gel using a 100 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 50:50 as eluents affording the title compound (2.9 g) as a colorless oil.
Workup
- customto give a colourless solution
- customThe reaction mixture was quenched with 10 ml of water
- additiondiluted with 10 ml of dichloromethane
- customTwo phases were separated through a separating funnel
- dry with materialThe organic phase was dried over Na2SO4
- customevaporated under vacuum
- customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 100 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 50:50 as eluents
Sources & evidence
- ORD record
- ord-9226d8afff3d42e8b7ab4bf50c8ab51f
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346790B2
Reaction notes
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