Acetone → 1-(Pyridin-2-yl)butane-1,3-dione
Reaction equation
C[O-].[Na+].[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([O:12]C)=O.[CH3:14][C:15]([CH3:17])=[O:16]>O1CCCC1>[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])[CH2:14][C:15](=[O:16])[CH3:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A sodium methoxide solution (28% in methanol) was added dropwise to a mixture of 10 g (73 mmol) methyl picolinate and 25 ml (124 mmol) of acetone in 150 ml of tetrahydrofuran. The mixture was stirred at 20° C. for 3 hours and the solvent was removed under reduced pressure. The residue was taken up in water, acidified with 2 molar aqueous hydrochloric acid and extracted with dichloromethane. Drying of the combined organic phases and removal of the solvent under reduced pressure gave 7.940 g of product (60% of theory); NMR (CDCl3, 400 MHz): 2.23 (s, 3H); 6.81 (s, 1H); 7.41 (m, 1H); 7.83 (m, 1H); 8.09 (m, 1H); 8.68 (m, 1H); 15.7 (br, 1H).
Workup
- customthe solvent was removed under reduced pressure
- extractionextracted with dichloromethane
- customDrying of the combined organic phases and removal of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-2ba512d3505e4f05897ac8a377681c17
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067611B2
Reaction notes
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