HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Imidazole → (16-Bromohexadecyloxy)-t-butyldimethylsilane

HRID 1367770
Notes
Print preview

Reaction equation

HRID 1367770 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 275701316-Bromo-1-hexadecanol

Product 1

HCID 86627057(16-Bromohexadecyloxy)-t-butyldimethylsilaneYield 81%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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

  1. extractionwas then extracted three times with dichloromethane
  2. washThe organic layer was washed with saline solution
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07893304B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes