Toluene → HCID 22248495, compound

HRID 914854Notes

Reaction equation

HRID 914854 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=[O:9].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Br)C1C=CC=CC=1>[CH2:22]([N:13]1[CH2:12][CH:11]=[C:10]([CH:8]([OH:9])[CH2:7][C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])[CH2:15][CH2:14]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 22247946HCID 22247946, compound

Product 1

HCID 22248495HCID 22248495, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 7498Benzyl BromideSolvent

Conditions

Temperature
110 °C

Procedure

After dissolving 2.72 g of 2-(3-methyl-2-thienyl)-1-(4-pyridyl)ethanone in 15 ml of toluene, 1.79 ml of benzyl bromide was added, the mixture was stirred for 7 hours at 110° C. and the precipitate was filtered out. The filtered substance was dissolved in 60 ml of methanol, 1.42 g of sodium borohydride was added in small portions at a time while cooling on ice, and the mixture was stirred for 1 hour. The reaction solution was distilled off under reduced pressure, water was added, and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (2.85 g, 73% yield).

Workup

  1. additionwas added
  2. filtrationthe precipitate was filtered out
  3. dissolutionThe filtered substance was dissolved in 60 ml of methanol
  4. addition1.42 g of sodium borohydride was added in small portions at a time
  5. temperaturewhile cooling on ice
  6. stirringthe mixture was stirred for 1 hour
  7. distillationThe reaction solution was distilled off under reduced pressure, water
  8. additionwas added
  9. extractionextraction
  10. washThe organic layer was washed with water and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9740ba2cc56e448d98e02670639f1cca
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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