Imidazole → HCID 15340873, compound

HRID 1608760Notes

Reaction equation

HRID 1608760 reaction equation
[C:1]1([S:7]([CH2:10][C@H:11]([C:13]2([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH3:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.Cl[Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27]>CN(C)C=O>[C:1]1([S:7]([CH2:10][C@H:11]([C:13]2([O:18][Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH3:12])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 22858127HCID 22858127, compound

Product 1

HCID 15340873HCID 15340873, compoundYield 123.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6a (2.40 g, 8.94 mmol) and imidazole (1.22 g, 17.9 mmol) in N,N-dimethylformamide (20 mL) was added chlorotriethylsilane (2.2 mL, 13.1 mmol) in one portion. The mixture was stirred at ambient temperature for 3d. The mixture was poured into ice water, and extracted with diethyl ether. The combined organic layers were washed with water and brine, and dried over sodium sulfate. Filtration and concentration gave 4.24 g of an oily material, which was purified by column chromatography (silica gel 40 g, ethyl acetate in n-hexane, 10%) to give 3.67 g (quantitative) of 7a, as a colorless oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-cf72e42b44a34003954b024d4ce0590a
Source dataset
uspto-grants-1995_03
Patent number
US05397775

Reaction notes

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