Phenethyl bromide → 1,3-Diethyl 2-(2-phenylethyl)propanedioate
Reaction equation
CC(C)([O-])C.[K+].[C:7]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH2:18](Br)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:16]([O:15][C:7]([CH:8]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:14])[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
123.4 g of potassium tert-butoxide were added in portions, at a temperature of 15° C., to a solution of 160.1 g of diethyl malonate in one litre of dimethylformamide. The reaction mixture was stirred for 30 minutes and a solution of 207.7 g of phenethyl bromide in 200 ml of dimethylformamide was then added dropwise at room temperature. The reaction mixture was subsequently heated at 60° C. for one hour and then allowed to cool down once again. The dimethylformamide was evaporated off under reduced pressure and the remaining residue was taken up in a mixture of methyl tert-butyl ether and water. The organic phase was separated, washed with water, dried over sodium sulfate and evaporated. The crude product, which remained as an oily residue, was purified by distillation under reduced pressure. 202.5 g of ethyl 2-ethoxycarbonyl-4-phenylbutanoate were obtained, b.p.1.5 =148°-153° C.
Workup
- temperatureto cool down once again
- customThe dimethylformamide was evaporated off under reduced pressure
- additionthe remaining residue was taken up in a mixture of methyl tert-butyl ether and water
- customThe organic phase was separated
- washwashed with water
- dry with materialdried over sodium sulfate
- customevaporated
- distillationwas purified by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-f315c58361c9445ab2ad7f279caf5f02
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05783573
Reaction notes
Loading…