Reaction equation
[Li].[CH3:2][CH2:3][C:4](=[O:10])[CH2:5][C:6](=[O:9])[CH2:7][CH3:8].CN(C)C(=O)N(C)C.[CH2:19]([C:21](=[CH:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]2[O:34][CH2:35][O:36][C:30]=2[CH:29]=1)[CH2:22][CH2:23]I)[CH3:20]>>[CH2:19]([C:21](=[CH:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]2[O:34][CH2:35][O:36][C:30]=2[CH:29]=1)[CH2:22][CH2:23][CH:5]([C:4](=[O:10])[CH2:3][CH3:2])[C:6](=[O:9])[CH2:7][CH3:8])[CH3:20]Participants
Procedure
A solution of 15 g. of the lithium salt of 3,5-heptanedione (prepared as described in Example 8 below) in 100 ml. of tetramethylurea was stirred under nitrogen at room temperature, and 10 g. of 3-ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl iodide (Preparation D1) was added. The reaction mixture was stirred for forty-eight hours, then concentrated to remove the solvent, and the residue slurried in ether and treated with excess glacial acetic acid. Water was added, the ether layer separated, washed with water and concentrated. The residue was distilled in a molecular still to remove volatile material at 110° C. (0.001 mml.), and the non-volatile residue was chromatographed on 10 g. of activated magnesium silicate in benzene solution and eluted with ethyl acetate to give 4-[3-ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl]-3,5-heptanedione as a yellow oil.
Workup
- concentrationconcentrated
- customto remove the solvent
- additionthe residue slurried in ether and treated with excess glacial acetic acid
- additionWater was added
- customthe ether layer separated
- washwashed with water
- concentrationconcentrated
- distillationThe residue was distilled in a molecular still
- customto remove volatile material at 110° C. (0.001 mml.)
- customthe non-volatile residue was chromatographed on 10 g
- washof activated magnesium silicate in benzene solution and eluted with ethyl acetate
Sources & evidence
- ORD record
- ord-e01a204d32824ab3a4304798e5cd17ea
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04171378
Linked notes
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