Acetic Acid → (Benzylamino)acetaldehyde diethyl acetal

HRID 554720Notes

Reaction equation

HRID 554720 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13][NH2:14])[CH3:10].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([NH:14][CH2:13][CH:12]([O:15][CH2:16][CH3:17])[O:11][CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 695242,2-DiethoxyethylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 521961(Benzylamino)acetaldehyde diethyl acetal

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Benzaldehyde (1.27 g, 12 mmol) in MeOH (50 mL) was added aminoacetaldehyde diethyl acetal (1.75 mL, 12 mmol) and acetic acid (1.03 mL, 18 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was added to a stirred solution of sodium cyanoborohydride (816 mg, 13 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated under reduced pressure. Then H2O and ethyl acetate were added to the reaction mixture. The organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. The crude compound was used next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThen H2O and ethyl acetate were added to the reaction mixture
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customwithout further purification

Sources & evidence

ORD record
ord-ddfaa3fe1e4c4545b5bb29eed5a72425
Source dataset
uspto-grants-2011_11
Patent number
US08049008B2

Reaction notes

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