Diethylamine → N,N-diethyl-4,4-dimethoxy-3-methyl-2-butenylamine
Reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]([CH3:11])=[CH:5][CH2:6]OC(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:33]([N:35]([CH2:6][CH:5]=[C:4]([CH3:11])[CH:3]([O:2][CH3:1])[O:12][CH3:13])[CH2:36][CH3:37])[CH3:34]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 56.4 g (0.30 mol) of 4-acetoxy-2-methyl-2-butenal dimethyl acetal, 150 ml of diethylamine, 675 mg (3 mmol) of palladium (II) acetate and 3.9 g (15 mmol) of triphenylphosphine was boiled under reflux for 15 hours under argon. After concentrating the mixture, the residue was suspended in 170 ml of ether/pentane (1:1), the solution was treated with active carbon, filtered over Hyflo and concentrated. The residual oil was firstly distilled at 40°-55°/0.3 mmHg over a 5 cm Vigreux column, there being obtained 57.1 g of N,N-diethyl-4,4-dimethoxy-3-methyl-2-butenylamine as a 90:10 (E/Z) mixture. This mixture was then fractionated over a 30 cm packed column. There were firstly obtained a total of 34.8 g (58%) of mixed fractions [(E/Z)=86:14] and then 14.5 g (24%) of pure (E)-N,N-diethyl-4,4-dimethoxy-3-methyl-2-butenylamine of boiling point 30°-32°/0.06 mmHg.
Workup
- temperatureunder reflux for 15 hours under argon
- concentrationAfter concentrating the mixture
- additionthe solution was treated with active carbon
- filtrationfiltered over Hyflo
- concentrationconcentrated
- distillationThe residual oil was firstly distilled at 40°-55°/0.3 mmHg over a 5 cm Vigreux column
Sources & evidence
- ORD record
- ord-ed679a38f1584f48acdb859a27aa7de7
- Source dataset
- uspto-grants-1986_03
- Patent number
- US04578462
Reaction notes
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