Water → 3-Ethyl-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone
Reaction equation
C(O[C:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:7][C:6](=[O:23])[CH:5]=1)C.[CH2:24]([Li])[CH3:25].O>C1C=CC=CC=1>[CH2:24]([C:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:7][C:6](=[O:23])[CH:5]=1)[CH3:25]Participants
Procedure
A solution of 3-ethoxy-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone (2.0 g) in benzene (60 ml) was added dropwise with stirring in an atmosphere of dry nitrogen to an ice-cooled 1.5 M solution of ethyllithium in benzene (20.8 ml). When the addition was complete, water was added and the mixture was allowed to stand overnight at room temperature. The benzene layer was separated and the aqueous layer was extracted with ether. The organic solutions were combined, dried and the solvents were evaporated under reduced pressure. The residue was purified by preparative-layer chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (b.p. 60°-80°) for elution to afford the title compound (0.65 g) as a pale yellow oil. (Found: C, 70.9; H, 7.7. C18H24O4 requires C, 71.0; H, 7.9%.)
Workup
- additionWhen the addition
- customThe benzene layer was separated
- extractionthe aqueous layer was extracted with ether
- customdried
- customthe solvents were evaporated under reduced pressure
- customThe residue was purified by preparative-layer chromatography on silica gel using
- additiona mixture of ethyl acetate and petroleum ether (b.p. 60°-80°)
- washfor elution
Sources & evidence
- ORD record
- ord-c5fe46a367fe4ec0b1f2824a37ea6ece
- Source dataset
- uspto-grants-1982_02
- Patent number
- US04315006
Reaction notes
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