Imidazole → [(11-Bromoundecyl)oxy](tert-butyl)dimethylsilane

HRID 1440967Notes

Reaction equation

HRID 1440967 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][OH:13].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(OCC)C>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 7416311-Bromo-1-undecanol

Product 1

HCID 15086119[(11-Bromoundecyl)oxy](tert-butyl)dimethylsilaneYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

100 g of 11-bromoundecanol (Fluka) is dissolved in 240 ml of tetrahydrofuran and mixed at 25° C. with 58 g of imidazole as well as 74.3 g of tert-butyldimethylsilyl chloride in 80 ml of tetrahydrofuran and stirred for 2 hours at 25° C. For working up, 700 ml of diethyl ether is added, the precipitated hydrochloride is filtered off, evaporated to dryness in a vacuum and chromatographed on silica gel with hexane/toluene. 136.9 g of 11-bromoundecyl-tert-butyldimethylsilyl ether is obtained as oil.

Workup

  1. filtrationthe precipitated hydrochloride is filtered off
  2. customevaporated to dryness in a vacuum
  3. customchromatographed on silica gel with hexane/toluene

Sources & evidence

ORD record
ord-bb2d7ae8f63e4be4b83c104b9af06001
Source dataset
uspto-grants-1996_03
Patent number
US05502046

Reaction notes

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