Sodium ethoxide → 2-(4-Methylpyridin-2-yl)-5-(propan-2-yl)cyclohexane-1,3-dione
Reaction equation
[CH3:1][CH:2]([CH:4]([CH2:11][C:12](=[O:21])[CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1)[CH2:5][C:6]([O:8]CC)=O)[CH3:3].[O-]CC.[Na+]>>[CH3:3][CH:2]([CH:4]1[CH2:5][C:6](=[O:8])[CH:13]([C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=2)[C:12](=[O:21])[CH2:11]1)[CH3:1]Participants
3
Procedure
The procedure of Example 2 was used to prepare the title compound from ethyl 3-(1-methylethyl)-6-(4-methyl-2-pyridinyl)-5-oxohexanoate and sodium ethoxide using a 2 hour reflux period in ethanol. The product was liberated as an oil from the aqueous phase by adjusting the pH to about 5 and recovered by ether extraction. The ether extract was worked up giving a semi-solid which was recrystallized successively from ethyl acetate and isopropyl ether giving the product as a solid, mp 104.5°-106.5° C. The confirmatory elemental analysis is shown in Table II.
Sources & evidence
- ORD record
- ord-4b56fdc9d2944dbc92ae571727fec6ff
- Source dataset
- uspto-grants-1987_07
- Patent number
- US04678501
Reaction notes
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