Imidazole → HCID 67130720, compound

HRID 2046794Notes

Reaction equation

HRID 2046794 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([OH:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1.N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCOC(C)=O>CN(C=O)C.O>[Si:27]([O:8][CH:6]1[CH2:7][CH:2]([CH3:1])[CH2:3][C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[CH:5]1)([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 671307105-Methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol

Product 1

HCID 67130720HCID 67130720, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (1.0 equiv.) in DMF (0.5 M) was added imidazole (4.0 equiv.) and TBDMSCl (2.5 equiv.). After stirring for 18 hours the solution was portioned between EtOAc and H2O and separated. After washing further with H2O (3×) and NaCl(sat.), drying over MgSO4, filtering and removal of solvents, 4-(3-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl)-3-nitropyridine was obtained (85%). LC/MS=349.2 (M+H), LC=5.99 min.

Workup

  1. customseparated
  2. washAfter washing further with H2O (3×) and NaCl(sat.)
  3. dry with materialdrying over MgSO4
  4. filtrationfiltering
  5. customremoval of solvents

Sources & evidence

ORD record
ord-2910c9ae3aa04357982592a99affa1f7
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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