Benzaldehyde → (Benzylamino)acetaldehyde diethyl acetal

HRID 576864Notes

Reaction equation

HRID 576864 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[BH-](OC(=O)C)OC(=O)C)(=O)C>O1CCCC1.C(OCC)(=O)C>[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 3

HCID 240BenzaldehydeHCID 695242,2-DiethoxyethylamineHCID 2724942Triacetoxyborohydride

Product 1

HCID 521961(Benzylamino)acetaldehyde diethyl acetalYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzaldehyde 5.1 ml (50.0 mmol) in 2,2-diethoxyethanamine 10.9 ml (75.0 mmol) was stirred at room temperature for 0.5 hour. The reaction mixture was diluted with tetrahydrofuran 450 ml and triacetoxyborohydride 32.0 g (150 mmol) was added and the mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate 500 ml and washed with saturated sodium bicarbonate 500 ml, water 500 ml and brine 500 ml. The organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=70:30 to 50:50) to obtain the title compound 7.8 g (yield 70%).

Workup

  1. additionwas added
  2. washwashed with saturated sodium bicarbonate 500 ml, water 500 ml and brine 500 ml
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=70:30 to 50:50)

Sources & evidence

ORD record
ord-1952e2c14c2e4932a9a22d8ce7bacc9c
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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