Benzaldehyde → HCID 19600250, compound

HRID 611239Notes

Reaction equation

HRID 611239 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][NH2:8])=[CH:2]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+].[OH-].[Na+]>CO>[CH2:9]([NH:8][CH2:7][CH2:6][C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 157218442-(furan-3-yl)ethan-1-amine

Product 1

HCID 19600250HCID 19600250, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the above crude 2-(3-furyl)ethylamine and 4.24 g (39.9 mmol) of benzaldehyde in 50 ml of methanol was stirred at room temperature for 0.5 hours. The reaction mixture was cooled with ice-water; 1.89 g (49.9 mmol) of sodium borohydride was added portionwise followed by stirring at room temperature for 1 hour. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate) to yield the desired product.

Workup

  1. extractionextracted with dichloromethane 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-0d21e052c5ee4b5aac518ab9b0c1f518
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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