Pyridine → HCID 20068365, compound

HRID 1638258Notes

Reaction equation

HRID 1638258 reaction equation
N1C=CC=CC=1.ClCCl.[CH2:10]([CH:12]([C:14]1[N:18]([CH:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21][CH2:20]2)[CH:17]=[N:16][CH:15]=1)[OH:13])[CH3:11]>[O-2].[Cr+6].[O-2].[O-2].O>[CH:19]1([N:18]2[C:14]([C:12](=[O:13])[CH2:10][CH3:11])=[CH:15][N:16]=[CH:17]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 20068382HCID 20068382, compound

Product 1

HCID 20068365HCID 20068365, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

A solution of 42 parts of chromium(VI) oxide and 66 parts of pyridine in 665 parts of dichloromethane was stirred for 20 minutes at room temperature. A solution of 19 parts of α-ethyl-1-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazole-5-methanol in 13.3 parts of dichloromethane was added dropwise to the thus obtained mixture. Upon complete addition, stirring was continued for 4 hours at room temperature. The reaction mixture was poured into water and the layers were separated. The organic layer was washed twice with water and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was dried for a long time in vacuo at 100° C., yielding 2.2 parts (12.3%) of 1-[1-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazol-5-yl]-1-propanone as an oily residue (compound 2.53).

Workup

  1. additionUpon complete addition
  2. customthe layers were separated
  3. washThe organic layer was washed twice with water
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was dried for a long time in vacuo at 100° C.

Sources & evidence

ORD record
ord-df318cb6573942c4acb90ed89a3771b9
Source dataset
uspto-grants-1989_11
Patent number
US04878940

Reaction notes

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