Imidazole → HCID 131722274, compound

HRID 566716Notes

Reaction equation

HRID 566716 reaction equation
N1[CH:6]=[CH:5][C:4]([CH2:7]O)=[CH:3]C=1.N1[CH:13]=[CH:12][N:11]=[CH:10]1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])(C)C.CN(C=[O:26])C>>[C:17]([SiH2:14][O:26][C:4]([CH3:3])([CH3:7])[C:5]1[CH:6]=[CH:10][N:11]=[CH:12][CH:13]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 114724-HydroxymethylpyridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 131722274HCID 131722274, compound

Procedure

To a stirred solution of 4-pyridylcarbinol (21.8 g, 0.20 mole) in DMF (200 mL) at 25° C. was added imidazole (15.64 g, 0.23 mole) and t-butyldimethylsilyl chloride (31.65 g, 0.21 mole). The reaction mixture was allowed to stirred at that temperature for 3 hr. Standard aqueous work up (ethyl acetate extraction, washed with water and brine, dried with MgSO4, evaporation), followed by chromatographic purification (silica gel, hexane/ethyl acetate) gave the title compound. 1H-NMR (CDCl3, 400 MHz) δ: 8.50(d, 2H), 7.25(d, 2H), 4.86(s, 2H), 0.90(s, 9H), 0.05(s, 6H).

Workup

  1. extractionStandard aqueous work up (ethyl acetate extraction, washed with water and brine, dried with MgSO4, evaporation)
  2. customfollowed by chromatographic purification (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-91142fa4979e47cba2a202f4056d2576
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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