Ethyl 5-methyl-2-(prop-1-en-2-yl)hex-4-enoate → HCID 11041681, compound
Reaction equation
CC(C)([O-])C.[K+].[C:7]([CH:10]([CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:9])=[CH2:8]>O1CCCC1>[C:7](=[C:10]([CH2:16][CH:17]=[C:18]([CH3:19])[CH3:20])[C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:9])[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In a nitrogen atmosphere, 3.5 g of potassium t-butoxide was added to a mixture of 38.3 g of al 8.2:81.8 mixture of ethyl 2-isopropenyl-5-methyl-4-hexenoate obtained in Synthesis Example 3 and ethyl 2-isopropylidene-5-methyl-4-hexenoate and 150 ml of tetrahydrofuran at room temperature, and stirred at room temperature overnight. After 60 g of a 25% aqueous solution of sodium hydroxide and 38 g of 99.5% ethanol were added thereto, the resulting mixture was heated to reflux for 7.5 hours with stirring, then subjected to addition of 100 g of a 25% aqueous solution of sodium hydroxide, and refluxed with stirring for further 15 hours. The reaction mixture was poured into ice water, followed by extraction with n-hexane. The extract was discarded. The aqueous phase was neutralized with 10% hydrochloric acid, followed by extraction with diethyl ether. The diethyl ether solution was subjected to typical work-up including washing, drying and concentration to obtain 31.47 g of crude product. The yield was 95.9%.
Sources & evidence
- ORD record
- ord-275c6a233b1b4852b11119825bf57b69
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126923B2
Reaction notes
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