Imidazole → HCID 57346940, compound

HRID 1374699Notes

Reaction equation

HRID 1374699 reaction equation
[Si:1](Cl)(C(C)(C)C)([CH3:3])[CH3:2].N1[CH:13]=[CH:12][N:11]=[CH:10]1.N1C=[CH:18][C:17]([CH2:20]O)=[CH:16]C=1.C([O:24][CH2:25][CH3:26])C.[CH3:27]N(C=O)C>>[C:17]([CH:25]([O:24][SiH:1]([CH3:3])[CH3:2])[C:26]1[CH:27]=[CH:10][N:11]=[CH:12][CH:13]=1)([CH3:20])([CH3:18])[CH3:16]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 114724-HydroxymethylpyridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 57346940HCID 57346940, compound

Procedure

To a stirred solution of tert-butyldimethylsilyl chloride (16.6 g, 0.11 mol) and imidazole (16.3 g, 0.24 mol) in DMF (20 mL) was added 4-pyridinemethanol (10 g, 0.09 mol) and the mixture was stirred for about 1 h. The reaction mixture was poured into diethyl ether (200 mL) and the resulting solution was washed with water (100 mL). The aqueous phase was extracted with diethyl ether and the combined organic phases are washed with water, brine and dried (MgSO4). The solvent was evaporated under reduced pressure to leave 4-(tertbutyidimethylsilyloxymethyl)pyridine, 22.5 g. 1H NMR (d6-DMSO) d 8.49 (d, 2H), 7.27 (d, 2H), 4.62 (s, 2H), 0.9 (s, 9H), 0.09 (s, 6H).

Workup

  1. washthe resulting solution was washed with water (100 mL)
  2. extractionThe aqueous phase was extracted with diethyl ether
  3. washthe combined organic phases are washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-846532c31b1648abbf03c0ad545f6604
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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