Acetaldehyde → 2-[2-(Diethylamino)ethoxy]ethanol

HRID 1838612Notes

Reaction equation

HRID 1838612 reaction equation
N[CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[BH3-][C:9]#[N:10].[Na+].[CH:12](=O)[CH3:13].[CH3:15]O>>[CH2:12]([N:10]([CH2:9][CH3:15])[CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])[CH3:13]

Participants

5

Reactant 4

HCID 177AcetaldehydeHCID 887MethanolHCID 13578DiglycolamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 673272-[2-(Diethylamino)ethoxy]ethanol

Conditions

Temperature
50 °C

Procedure

2-(2-aminoethoxy)ethanol (Aldrich 0.5 mmol) is treated with NaBH3CN (Aldrich, 200 mg, 3.0 mmol) in 50% aqueous methanol (30 mL). To this solution, acetaldehyde 95% purity (2 mL, 17 mmol) is added in one portion and the mixture is heated at 50° C. for 2 days in a flask under argon. After removal of the solvent under reduced pressure, the residue is dissolved in water, extracted with ethylacetate to give the title compound.

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. extractionextracted with ethylacetate

Sources & evidence

ORD record
ord-3e50f6b0e32c4502b87a5909e7d5fb8b
Source dataset
uspto-grants-2004_01
Patent number
US06673912B1

Reaction notes

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