Pyridine, hydrofluoride (1:1) → 4-Hydroxymethyl-1-(3-chlorophenyl)-1H-pyridin-2-one

HRID 2289640Notes

Reaction equation

HRID 2289640 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[CH:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10](=[O:21])[CH:9]=1)(C)(C)C.N1C=CC=CC=1.F.C(OC([O-])=O)([O-])=O.[Na+].[Na+]>C(#N)C>[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10](=[O:21])[CH:9]=1

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 22718997Sodium dicarbonateHCID 1317219134-(tert-butyl-dimethyl-silanyloxymethyl)-1-(3-chlorophenyl)-1H-pyridin-2-one

Product 1

HCID 186987734-Hydroxymethyl-1-(3-chlorophenyl)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(tert-butyl-dimethyl-silanyloxymethyl)-1-(3-chlorophenyl)-1H-pyridin-2-one (5.11 g, 14.6 mmol) in acetonitrile (75 ml) in a teflon beaker was added hydrogen fluoride-pyridine (2.5 ml, 87.5 mmol) and stirred for 3 hours. The reaction mixture was neutrallized with solid and aqueous sodium dicarbonate and then the solvent evaporated in vacuo. The resulting solid residue was extracted with EtOAc, dried (MgSO4), filtered and the solvent was evaporated in vacuo. This residue was chromatographed (silica gel, 80-100% EtOAc:hexane gradient elution) to afford the title compound.

Workup

  1. customthe solvent evaporated in vacuo
  2. extractionThe resulting solid residue was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated in vacuo
  6. customThis residue was chromatographed
  7. wash(silica gel, 80-100% EtOAc:hexane gradient elution)

Sources & evidence

ORD record
ord-d99367b4b0a44587a358a60bb6a1675b
Source dataset
uspto-grants-2000_07
Patent number
US06093737

Reaction notes

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