Imidazole → 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridine

HRID 426244Notes

Reaction equation

HRID 426244 reaction equation
C[C:2]1([CH2:8]O)[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1.N1C=CN=[CH:11]1.[C:15]([Si:19](C)(C)Cl)([CH3:18])([CH3:17])[CH3:16].CC[O:25][CH2:26][CH3:27]>CN(C=O)C>[C:15]([SiH2:19][O:25][C:26]([CH3:27])([CH3:11])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:8])[CH:7]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 1317294292-Methylpyridine methanol

Product 1

HCID 1317294284-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridineYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-methylpyridine methanol (3.39 g, 27.56 mmol) was stirred with imidazole (6.12 g, 90 mmol), and tert-butyldimethylchlorosilane (6.78 g, 45 mmol) in DMF 960 ml) at room temperature for overnight. The mixture was diluted with ether, washed with aqueous saturated sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:hexane (1:2)) to afford 5.9 g (90%) of 4-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-pyridine as a colorless oil. 1H NMR (200 MHz, CDCl3) δ0.11 (6H, s), 0.94 (9H, s), (3H, s), 2.52 (3H, s), 4.67 (2H, s), 6.97 (1H, d, J=6.7 Hz), 7.08 (1H, s), 8.10 (1H, d, J=6.7 Hz).

Workup

  1. washwashed with aqueous saturated sodium bicarbonate
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:2))

Sources & evidence

ORD record
ord-7996955ee0514b5bb32de88ac98e2655
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…