Acetic Acid → HCID 10612980, compound

HRID 554724Notes

Reaction equation

HRID 554724 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][NH2:18])[CH3:14].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][NH:18][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:3]=1[O:2][CH3:1])[CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 665812,3-DimethoxybenzaldehydeHCID 695242,2-DiethoxyethylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10612980HCID 10612980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,3-dimethoxybenzaldehyde (2 g, 12 mmol) in MeOH (50 mL) was added aminoacetaldehyde diethyl acetal (1.49 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 (829 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-84386c020e744dffba8907ff79d5c1a3
Source dataset
uspto-grants-2011_11
Patent number
US08049008B2

Reaction notes

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