Imidazole → HCID 77676860, compound

HRID 394955Notes

Reaction equation

HRID 394955 reaction equation
[CH3:1][C:2]12[CH:10]([CH:11]([CH3:19])[CH:12]=[CH:13][CH:14]([CH3:18])[CH:15]([CH3:17])[CH3:16])[CH2:9][CH2:8][CH:7]1[CH:6]([OH:20])[CH2:5][CH2:4][CH2:3]2.N1C=CN=C1.Cl[Si:27]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:28][CH3:29]>CN(C)C=O>[CH3:1][C:2]12[CH:10]([CH:11]([CH3:19])[CH:12]=[CH:13][CH:14]([CH3:18])[CH:15]([CH3:16])[CH3:17])[CH2:9][CH2:8][CH:7]1[CH:6]([O:20][Si:27]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:28][CH3:29])[CH2:5][CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 57358244HCID 57358244, compound

Product 1

HCID 77676860HCID 77676860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.95 g of [1R-[1α[1R*,4S*-(E)],3aβ,4α,7aα]]-octahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-1H-inden-4-ol 1 is introduced into 220 ml of dimethylformamide [H. H. Inhoffen et al. Chem. Ber. 91, 781 (1958)], 5.33 g of imidazole and 10.78 ml of chlorotriethylsilane are added, and it is stirred for 24 hours at room temperature. It is quenched with sodium chloride solution, extracted with ethyl acetate, the organic phase is washed with sodium chloride solution and dried on sodium sulfate. After the solvent is removed, the residue is purified by chromatography on silica gel with ethyl acetate/hexane, whereby 14.6 g of title compound 2 is obtained as a colorless oil.

Workup

  1. additionare added
  2. customIt is quenched with sodium chloride solution
  3. extractionextracted with ethyl acetate
  4. washthe organic phase is washed with sodium chloride solution
  5. customdried on sodium sulfate
  6. customAfter the solvent is removed
  7. customthe residue is purified by chromatography on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-0fd0da99013f4b538ee7d074c540f85e
Source dataset
uspto-grants-2003_08
Patent number
US06603031B1

Reaction notes

Loading…