Iodoethane → 5-Ethyl-2-methoxy-3,4-dimethyl-2-cyclopenten-1-one
Reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][C:10](=[O:21])[CH:11]([CH:16]([CH3:20])[C:17]([CH3:19])=O)[C:12](OC)=O.C(I)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C.O>[CH2:12]([CH:11]1[C:10](=[O:21])[C:9]([O:8][CH3:7])=[C:17]([CH3:19])[CH:16]1[CH3:20])[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
22.80 g (165 mmol) of potassium carbonate and 0.69 g (3 mmol) of benzyltriethylammonium chloride are suspended in 150 ml of acetonitrile. While stirring 32.42 g (150 mmol) of methyl 4-methoxy-2-(1-methylacetonyl)-acetoacetate are added thereto and the mixture is heated to 60° C. 28.08 g (180 mmol) of ethyl iodide are added thereto within 100 minutes and the mixture is stirred at 60° C. for a further 90 hours. The suspension is then poured into a solution of 10.35 g (75 mmol) of potassium carbonate in 450 ml of water and heated at reflux temperature for 30 hours. The cooled reaction solution is extracted 3 times with 300 ml of CH2Cl2. The combined organic phases are dried over magnesium sulphate and concentrated on a rotary evaporator. The crude product is distilled at 20 mbar/97°-99° C. and gives 3.61 g (14.3%) of 5-ethyl-2-methoxy-3,4-dimethyl-2-cyclopenten-1-one.
Workup
- additionare added
- temperatureheated
- temperatureat reflux temperature for 30 hours
- customThe cooled reaction solution
- extractionis extracted 3 times with 300 ml of CH2Cl2
- dry with materialThe combined organic phases are dried over magnesium sulphate
- concentrationconcentrated on a rotary evaporator
- distillationThe crude product is distilled at 20 mbar/97°-99° C.
Sources & evidence
- ORD record
- ord-b225a3a9c12f465f9164d7edf29c1239
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04892966
Reaction notes
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