Tetrabutylammonium Fluoride → 1-(4-hydroxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl)ethanone

HRID 2273305

Reaction equation

HRID 2273305 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:33](=[O:35])[CH3:34])[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:18][CH2:19][C:20]1[N:21]=[C:22]([C:33](=[O:35])[CH3:34])[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:24]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 71087685HCID 71087685, compound

Product 1

HCID 710869721-(4-hydroxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl)ethanoneYield 108.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound obtained in (2) (24.4 g) was dissolved in THF (200 mL), tetrabutylammonium fluoride (hereinafter sometimes referred to as TBAF) (a 1.0 M THF solution, 62.7 mL) was added under stirring, and stirring was continued for 1 hour. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%→100%) using an amino column (trade name: Hi-Flash Column 5L Amino, manufactured by Yamazen Corporation) to give the title compound (14.1 g).

Workup

  1. additionwas added
  2. stirringstirring
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%→100%)

Sources & evidence

ORD record
ord-be9491f77dfe4d37ad5c878abb97daf5
Source dataset
uspto-grants-2015_09
Patent number
US09120835B2

Linked notes

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