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

HRID 242372

Reaction equation

HRID 242372 reaction equation
[CH2:1]([O:3][CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][O:11][Si](CC)(CC)CC)[N:7]=[C:6]1[C:19](=[O:21])[CH3:20])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:3][CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][OH:11])[N:7]=[C:6]1[C:19](=[O:21])[CH3:20])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 710871971-[1-Ethoxymethyl-4-(triethylsilyloxymethyl)-1H-imidazol-2-yl]ethanone

Product 1

HCID 682719271-(1-Ethoxymethyl-4-hydroxymethyl-1H-imidazol-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (520 mg) obtained in (4) was dissolved in THF (10 mL), followed by addition of tetrabutylammonium fluoride (TBAF, 1.0 M THF solution, 3.32 mL) under stirring, and the 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 amino column (product name: SNAP Cartridge KP-NH 55 g, manufactured by Biotage, Ltd.) to afford the title compound (288 mg).

Workup

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

Sources & evidence

ORD record
ord-6d331297395d4da8b63cfab11b23c446
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Linked notes

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