Imidazole → HCID 66718395, compound

HRID 2096700Notes

Reaction equation

HRID 2096700 reaction equation
N1C=CN=C1.[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:17])([CH3:16])[CH3:15])[N:9]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:18]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:17])([CH3:15])[CH3:16])[N:9]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 191043162-(6-(Hydroxymethyl)pyridin-2-yl)propan-2-ol

Product 1

HCID 66718395HCID 66718395, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (2.27 g, 33.3 mmol) was added to a stirred solution of 2-hydroxymethyl-6-(1-hydroxy-1-methylethyl)pyridine (5.30 g, 31.7 mmol) and tert-butyldimethylsilylchloride (5.02 g, 33.3 mmol) in DMF (70 mL) and the mixture was stirred for 16 h at room temperature. The mixture was poured onto water, extracted with EtOAc, the organic portion was separated, dried (MgSO4), filtered and evaporated to give the title compound (8.19 g, 92%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.74-7.70 (1H, m), 7.40-7.38 (1H, m), 7.20-7.18 (1H, m), 5.34 (1H, s), 4.83 (2H, s), 1.52 (6H, s), 0.97 (9H, s), 0.13 (6H, s); (M+H)+ 282.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with EtOAc
  3. customthe organic portion was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0ace119b5fbf4429a0455e0bd9e69314
Source dataset
uspto-grants-2013_05
Patent number
US08450328B2

Reaction notes

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