Imidazole → HCID 86748316, compound

HRID 1492317Notes

Reaction equation

HRID 1492317 reaction equation
[C:1]1([S:7]([CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][C:12]2([CH3:17])[OH:16])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.Cl[Si](CC)(CC)CC.N1C(C)=CC=CC=1C.FC(F)(F)S([O:44][Si:45]([CH2:50][CH3:51])([CH2:48][CH3:49])[CH2:46][CH3:47])(=O)=O>C(Cl)Cl>[CH3:17][C:12]1([OH:16])[CH2:13][CH2:14][CH2:15][CH:11]1[CH2:10][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([S:7]([CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][C:12]2([CH3:17])[O:44][Si:45]([CH2:46][CH3:47])([CH2:48][CH3:49])[CH2:50][CH3:51])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 795ImidazoleHCID 79372,6-LutidineHCID 13819ChlorotriethylsilaneHCID 2733308Triethylsilyl trifluoromethanesulphonate2×HCID 86748315HCID 86748315, compound

Product 2

HCID 86748316HCID 86748316, compoundHCID 86748317HCID 86748317, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10a (2.69 g, crude) and imidazole (5.6 g, 82.3 mmol) in CH2Cl2 (50 mL) was added chlorotriethylsilane (1.7 mL, 10.1 mmol), and the mixture was stirred at ambient temperature overnight. To the mixture were added 2,6-lutidine (1.9 mL, 16.3 mmol) and triethylsilyl trifluoromethanesulfonate (1.9 mL, 8.40 mmol), and the mixture was stirred at ambient temperature for 35 min, then heated under reflux. Heating and stirring were continued with further addition of triethylsilyl trifluoromethanesulfonate (0.8 mL) overnight. Ice was added to the mixture, and the organic layer was separated. The aqueous layer was extracted with n-hexane, and the combined organic layers were washed with cold diluted HCl , water, NaHCO3 solution and NaCl solution, and dried over Na2SO4. Filtration and concentration, followed by chromatographic purification (SiO2 gel 50 g, EtOAc in n-hexane 5%), to give 3.21 g (quantitative yield from 9a) of 11a, as a colorless oil.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 35 min
  2. temperatureheated
  3. temperatureunder reflux
  4. temperatureHeating
  5. stirringstirring
  6. additionIce was added to the mixture
  7. customthe organic layer was separated
  8. extractionThe aqueous layer was extracted with n-hexane
  9. washthe combined organic layers were washed with cold diluted HCl , water, NaHCO3 solution and NaCl solution
  10. dry with materialdried over Na2SO4
  11. filtrationFiltration and concentration
  12. customfollowed by chromatographic purification (SiO2 gel 50 g, EtOAc in n-hexane 5%)

Sources & evidence

ORD record
ord-e3de16a316e34396872b9f4f2d5925f1
Source dataset
uspto-grants-1994_12
Patent number
US05373004

Reaction notes

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