Imidazole → 3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

HRID 85194Notes

Reaction equation

HRID 85194 reaction equation
N1C=CN=C1.[C:6]([Si:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)Cl)([CH3:9])([CH3:8])[CH3:7].[OH:24][CH2:25][C:26]1[C:27](=[O:32])[NH:28][CH:29]=[CH:30][CH:31]=1.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Si:10]([O:24][CH2:25][C:26]1[C:27](=[O:32])[NH:28][CH:29]=[CH:30][CH:31]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 106304823-(Hydroxymethyl)pyridin-2(1H)-one

Product 1

HCID 594101563-({[tert-Butyl(diphenyl)silyl]oxy}methyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

At RT, 0.65 g (9.59 mmol) of imidazole, 2.42 g (8.79 mmol) of t-butyldiphenylchlorosilane and 0.10 g (0.80 mmol) of DMAP are added to 1.00 g (7.99 mmol) of the compound from Example 2A in 19 ml of DMF, and the mixture is stirred for 18 h. 180 ml of water are then added, and the mixture is kept at 0° C. for 3 h. After filtration, the residue obtained is purified by chromatography on silica gel (ethyl acetate/ethyldimethylamine 1000:1). This gives 801 mg (27% of theory) of the desired compound.

Workup

  1. waitthe mixture is kept at 0° C. for 3 h
  2. filtrationAfter filtration
  3. customthe residue obtained
  4. customis purified by chromatography on silica gel (ethyl acetate/ethyldimethylamine 1000:1)

Sources & evidence

ORD record
ord-3432e846829744169702bc91a1fe99c8
Source dataset
uspto-grants-2014_09
Patent number
US08846934B2

Reaction notes

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