Acetic Acid → HCID 68271782, compound

HRID 242391Notes

Reaction equation

HRID 242391 reaction equation
[C:1]([C:4]1[N:5]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:6]=[C:7]([CH2:9][O:10][Si](C(C)(C)C)(C)C)[N:8]=1)(=[O:3])[CH3:2].C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([C:4]1[N:5]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:6]=[C:7]([CH2:9][OH:10])[N:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 71105123HCID 71105123, compound

Product 1

HCID 68271782HCID 68271782, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2-Dimethylpropionic acid [2-acetyl-4-(tert-butyldimethylsilyloxymethyl)imidazol-1-yl]methylester (1.50 g) was dissolved in THF (50 mL), and at room temperature acetic acid (1 mL) and TBAF (1.0 M THF solution, 4.97 mL) were added, followed by stirring for 4 hours. The reaction solution was concentrated, and the resulting residue was purified by flash chromatography (ethyl acetate/hexane=100%→100%) using silica gel column (product name: Hi-Flash Column 3 L, manufactured by Yamazen Corporation) to afford the title compound (1.10 g).

Workup

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

Sources & evidence

ORD record
ord-34222413cad34238bfa677ab77b94f51
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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