Water → HCID 19772265, compound

HRID 1614667Notes

Reaction equation

HRID 1614667 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1.Cl[CH2:16][C:17]1[N:22]=[C:21]([CH:23]=[O:24])[CH:20]=[CH:19][CH:18]=1.O>CS(C)=O.O1CCCC1>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:16][C:17]2[N:22]=[C:21]([CH:23]=[O:24])[CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1040094-(4-Methylphenyl)butanolHCID 197722996-(Chloromethyl)pyridine-2-carbaldehyde

Product 1

HCID 19772265HCID 19772265, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of 1.1 g of 60% sodium hydride in 30 ml of dimethyl sulfoxide under stirring at 70° C. for 30 minutes was added 4.1 g of 4-(4-methylphenyl)butanol at room temperature and stirred for 30 minutes. To a mixture was added 40 ml of tetrahydrofuran and was cooled at 0° C. To the resulting mixture was added dropwise a solution of 3.9 g of 6-chloromethyl-2-formylpyridine in 40 ml of tetrahydrofuran. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes and further was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give a residue as an oily substance. The residue was purified by column chromatography on silica gel by passing chloroform and methanol(100:1 ) to give 1.3 g of 6-[4-(4-methylphenyl) butoxy]methyl-2-formylpyridine.

Workup

  1. stirringstirred for 30 minutes
  2. temperaturewas cooled at 0° C
  3. additionAfter completion of the addition
  4. stirringthe mixture was stirred at the same temperature for 30 minutes
  5. stirringfurther was stirred at room temperature for 4 hours
  6. customAfter completion of the reaction
  7. extractionextracted with ethyl acetate
  8. washwashed with water
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customto give a residue as an oily substance
  12. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-136c25a4a02f4691a9da532e7621e3dd
Source dataset
uspto-grants-1993_03
Patent number
US05198452

Reaction notes

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