Tetrabutylammonium Fluoride → 1-[4-Hydroxymethyl-1-(2-propenyl)-1H-imidazol-2-yl]ethanone

HRID 242383Notes

Reaction equation

HRID 242383 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:28](=[O:30])[CH3:29])[N:23]([CH2:25][CH:26]=[CH2:27])[CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:18][CH2:19][C:20]1[N:21]=[C:22]([C:28](=[O:30])[CH3:29])[N:23]([CH2:25][CH:26]=[CH2:27])[CH:24]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 892622101-[4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-propenyl)-1H-imidazol-2-yl]ethanone

Product 1

HCID 866747321-[4-Hydroxymethyl-1-(2-propenyl)-1H-imidazol-2-yl]ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (0.750 g) obtained in (2) was dissolved in THF (50 mL), followed by addition of TBAF (1.0 M THF solution, 1.79 mL) under stirring, and the stirring was continued for 1 hour. The reaction solution was concentrated, and the resulting residue was purified by flash chromatography (ethyl acetate/hexane=5%-÷100%) using amino column (product name: Hi-Flash Column 3 L, manufactured by Yamazen Corporation), washed with ethyl acetate/hexane, and subsequently dried to afford the title compound (0.280 g).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe resulting residue was purified by flash chromatography (ethyl acetate/hexane=5%-÷100%)
  3. washwashed with ethyl acetate/hexane
  4. customsubsequently dried

Sources & evidence

ORD record
ord-c4e4ec8c1b1a4002a63874fea0b7400e
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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