Imidazole → HCID 86635919, compound

HRID 1798452Notes

Reaction equation

HRID 1798452 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 (1 eq.) from the previous step 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 ether/hexanes (1:1 v/v). 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 ether/hexanes (1:1 v/v)
  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-85c73a934cb9463587d56e4838e4da17
Source dataset
uspto-grants-2013_01
Patent number
US08343968B2

Reaction notes

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