Ethanol → 3-(N-ethylanilino)propane-1,2-diol
Reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[CH2:10]1[O:12][CH:11]1[CH2:13][OH:14].C(O)C>O>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:10][CH:11]([OH:12])[CH2:13][OH:14])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A mixture of N-ethylaniline (1.21 g, 10 mmol), glycidol (1.11 g, 15 mmol) and ethanol (1 ml) was heated by microwave irradiation for 10 min at 120° C. The mixture was dissolved in water (10 ml) and extracted with ethyl acetate (3 times 25 ml). The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by chromatography (SiO2, ethyl acetate/heptane=1:2) to yield a colorless liquid (1.85 g, 94%); MS (ISP): 196.3 ((M+H)+).
Workup
- extractionextracted with ethyl acetate (3 times 25 ml)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- customevaporated
- customThe residue was purified by chromatography (SiO2, ethyl acetate/heptane=1:2)
Sources & evidence
- ORD record
- ord-65dc4a37cbdf435abf34aacce9a0b5ef
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812047B2
Reaction notes
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