Acetic Acid → HCID 19600258, compound

HRID 611069Notes

Reaction equation

HRID 611069 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH:8]=O)=[CH:2]1.[CH2:10]([NH2:13])[CH:11]=[CH2:12].C(O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[CH2:10]([NH:13][CH2:8][CH2:7][CH2:6][C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[CH:11]=[CH2:12]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7853AllylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 110078933-FURAN-3-YL-PROPIONALDEHYDE

Product 1

HCID 19600258HCID 19600258, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the above crude 3-(3-furyl)propanal, 7.94 ml (106 mmol) of allylamine and 2.54 ml (42.3 mmol) of acetic acid in 100 ml of methanol, 1.33 g (21.2 mmol) of sodium cyanoborohydride was added at room temperature, followed by stirring at room temperature for 1 day. 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 (ethyl acetate to ethyl acetate/methanol=4/1) 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 (ethyl acetate to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-554e7a6213e74b8da1d331b4b8c7bcc1
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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