Imidazole → HCID 86635919, compound

HRID 561819Notes

Reaction equation

HRID 561819 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](/[CH:10]=[CH:11]/[CH2:12][O:13][CH3:14])[CH:9]=1)[CH:5]=[O:6].[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].N1C=CN=C1>CN(C=O)C>[Si:19]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](/[CH:10]=[CH:11]/[CH2:12][O:13][CH3:14])[CH:9]=1)[CH:5]=[O:6])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 574568653-Hydroxy-5-[(1E)-3-(methyloxy)-1-propen-1-yl]benzaldehyde

Product 1

HCID 86635919HCID 86635919, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-5-[(1E)-3-methoxyprop-1-en-1-yl]benzaldehyde from the previous step (1 eq.) and tert-butylchlorodimethylsilane (1 eq.) were combined in DMF (0.5 M). To this solution was then added imidazole (1.5 eq.) and the reaction mixture was stirred at RT for 16 h. The resulting solution was quenched with water and extracted with 1:1 (v:v) ether:hexanes. The combined organic extracts were washed with brine, dried over MgSO4 and filtered through a plug of SiO2. Concentration of the filtrate in vacuo afforded the title compound as a pale yellow oil.

Workup

  1. customThe resulting solution was quenched with water
  2. extractionextracted with 1:1 (v:v) ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a plug of SiO2

Sources & evidence

ORD record
ord-eda687d3ebab495dbb1063b871ca91a0
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

Loading…