Benzaldehyde → (Benzylamino)acetaldehyde diethyl acetal

HRID 1598475Notes

Reaction equation

HRID 1598475 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.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C.C(OCC)(=O)C.C(O)(=O)C>[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13][NH:14][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:10]

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 695242,2-DiethoxyethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 521961(Benzylamino)acetaldehyde diethyl acetal

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzaldehyde (3.0 mL, 0.0295 mol) and 2-aminoacetaldehyde diethyl acetal (4.3 mL, 0.0295 mol) in dichloroethane (60 mL) was brought to pH 7 by the addition of acetic acid. Sodium triacetoxyborohydride (8.1 g, 0.038 mol) was added and the reaction stirred until complete. Saturated sodium bicarbonate was added and the reaction stirred for 30 min. Ethyl acetate was added and the organic phase washed with saturated sodium chloride, then dried over magnesium sulfate. The crude product was chromatographed on silica gel with 30% ethyl acetate in hexane. The title compound was obtained as a pale yellow oil (2.93 g). NMR (CDCl3, 300 MHz) δ 7.31 (5H, m), 4.62 (1H, t, J=5 Hz), 3.81 (2H, s), 3.68 (2H, m), 3.54 (2H, m), 2.75 (2H d, J=5 Hz), 1.20 (6H, t, J=7 Hz).

Workup

  1. stirringthe reaction stirred for 30 min
  2. washthe organic phase washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product was chromatographed on silica gel with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-868e549ba226461c86cd20a9543d96fb
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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