Sodium ethoxide → Ethyl 6,6,6-trichloro-3,3-dimethyl-4-hexenoate
Reaction equation
Br[CH:2]([CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])[C:3]([CH3:11])([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[O-]CC.[Na+]>O1CCCC1>[Cl:14][C:13]([Cl:15])([Cl:16])[CH:12]=[CH:2][C:3]([CH3:10])([CH3:11])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Two milliliters of a solution of anhydrous tetrahydrofuran containing 709 mg (2 mmoles) of ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate was added dropwise to a suspension of 163 mg (2.4 mmoles) of sodium ethoxide in 20 ml of anhydrous tetrahydrofuran. The mixture was stirred at room temperature for about 16 hours, poured into ice water and extracted with diethyl ether. The extract was dried over magnesium sulfate and then distilled to give 448 mg (82% yield) of ethyl 6,6,6-trichloro-3,3-dimethyl-4-hexenoate, b.p. 83°-85°/0.1 mm.