Imidazole → HCID 53897948, compound

HRID 1613560Notes

Reaction equation

HRID 1613560 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2([C:14]([OH:17])([CH3:16])[CH3:15])[CH2:13][CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.Cl[Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26].C(OCC)C>CN(C)C=O>[C:1]1([S:7]([CH2:10][C:11]2([C:14]([O:17][Si:24]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:25][CH3:26])([CH3:15])[CH3:16])[CH2:13][CH2:12]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 13819ChlorotriethylsilaneHCID 54039813HCID 54039813, compound

Product 1

HCID 53897948HCID 53897948, compoundYield 126.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred and ice-cooled solution of 8 (4.05 g, 15.9 mmol) and imidazole (2.16 g, 31.7 mmol) in N,N-dimethylformamide was added chlorotriethylsilane (4 mL, 23.8 mmol), and the mixtrue was stirred at ambient temperature overnight. To the mixture was added ice and diethyl ether and the mixture was stirred at ambient temperature for 20 min. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 7.40 g of an oily material, which was purified by column chromatography (silica gel 70 g, 4-12% ethyl acetate in n-hexane) to give 5.89 g (quantitative) of 9, as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ: 0.55 (6H, q, J=7.9 Hz), 0.80(2H, dd, J=6.8 and 4.2 Hz), 0.91(9H, t, J=7.9 Hz), 0.92(2 H), 1.20 (6H, s), 3.39(2H, s), 7.55(2H, t, J=7.4 Hz), 7.64(1H, t, J=7.4 Hz), 7.89(2H, d, J=7.4 Hz)

Workup

  1. stirringthe mixtrue was stirred at ambient temperature overnight
  2. stirringthe mixture was stirred at ambient temperature for 20 min
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with diethyl ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-677a90a315304b919656116bb374e9a8
Source dataset
uspto-grants-1993_03
Patent number
US05194431

Reaction notes

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