Benzyl Bromide → HCID 67282870, compound

HRID 913012Notes

Reaction equation

HRID 913012 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([CH3:11])[C:5]=1[CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.CO>[CH2:18]([O:3][C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([CH3:11])[C:5]=1[CH:12]([OH:17])[C:13]([F:16])([F:14])[F:15])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 67282261HCID 67282261, compound

Product 1

HCID 67282870HCID 67282870, compoundYield 31.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of NaOH (1.77 g dissolved in 20 mL, 44.4 mmol) in de-ionized water was added dropwise to a suspension of 3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (9.00 g, 40.3 mmol) in methanol (100 mL), and followed by benzyl bromide (5.28 mL, 44.4 mmol) at room temperature. The resulting suspension was refluxed for 3.5 h, and then stirred at RT for overnight. Methanol was removed under vacuum using the rotary evaporator, and the residue was diluted with water and extracted two times with CH2Cl2 (2×100 mL). The combined organic fractions were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified by flash column chromatography on silica gel using a mixture of methanol and ethyl acetate (10/90, v/v) as eluant. Fractions rich in the product were pooled together and evaporated to dryness to give 4 g of 3-benzyloxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as a solid.

Workup

  1. temperatureThe resulting suspension was refluxed for 3.5 h
  2. customMethanol was removed under vacuum
  3. customthe rotary evaporator
  4. additionthe residue was diluted with water
  5. extractionextracted two times with CH2Cl2 (2×100 mL)
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by flash column chromatography on silica gel using
  11. additiona mixture of methanol and ethyl acetate (10/90
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-e40d4adfaba54625ba244d88a74528fb
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

Loading…