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

HRID 1885555Notes

Reaction equation

HRID 1885555 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 200.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

175 g of 11-bromoundecanol (Fluka) is dissolved in 420 ml of tetrahydrofuran and combined at 25° with 101 g of imidazole as well as 130.1 g of tert-butyldimethylsilyl chloride in 140 ml of tetrahydrofuran, and agitated for 2 hours at 25°. For the working up step, 1.2 1 of diethyl ether is added, the thus-precipitated hydrochloride is filtered off, the mixture concentrated to dryness under vacuum and chromatographed on silica gel with hexane/ethyl acetate, yielding 509.6 g of 11-bromoundecyl-tert-butyldimethylsilyl ether as an oil.

Workup

  1. filtrationthe thus-precipitated hydrochloride is filtered off
  2. concentrationthe mixture concentrated to dryness under vacuum
  3. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-0b1f262df7234abd9400fc4a8ad0fa49
Source dataset
uspto-grants-1992_09
Patent number
US05145847

Reaction notes

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