Imidazole → HCID 66718395, compound

HRID 876995Notes

Reaction equation

HRID 876995 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 91.8%

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 To) 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-551a58b4f00e4bc2b82249d86bcdf961
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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