Imidazole → (16-Bromohexadecyloxy)-t-butyldimethylsilane
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].[Cl-].[NH4+]>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]Participants
6
Procedure
16-Bromohexadecan-1-ol (1 g) was dissolved in 20 ml of dichloromethane, and imidazole (317.9 mg) and t-butyldimethylsilyl chloride (701.4 mg) were added to this solution. The reaction mixture was stirred at room temperature for four hours. Saturated ammonium chloride solution was added to the reaction mixture, which was then extracted three times with dichloromethane. The organic layer was washed with saline solution and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (heptane:ethyl acetate=7:3) gave (16-bromohexadecyloxy)-t-butyldimethylsilane as a colorless oil at an 81% yield.
Workup
- extractionwas then extracted three times with dichloromethane
- washThe organic layer was washed with saline solution
- dry with materialdried over magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customPurification of the residue by silica gel flash chromatography (heptane:ethyl acetate=7:3)
Sources & evidence
- ORD record
- ord-2280bb53a1af4e60b369dd078465c9a8
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893304B2
Reaction notes
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