Thionyl Chloride → Pyriofenone
Reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[C:8]([O:15][CH3:16])=[N:9][CH:10]=[C:11]([Cl:14])[C:12]=1[CH3:13].[Cu]C#N.[Cl-].[Li+].[CH3:22][O:23][C:24]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[C:29]([CH3:37])[C:25]=1[C:26](Cl)=[O:27].COC1C(OC)=C(OC)C=C(C)C=1C(O)=O.S(Cl)(Cl)=O>>[CH3:22][O:23][C:24]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[C:29]([CH3:37])[C:25]=1[C:26]([C:7]1[C:8]([O:15][CH3:16])=[N:9][CH:10]=[C:11]([Cl:14])[C:12]=1[CH3:13])=[O:27]Participants
Reactant 7
Product 1
Procedure
(b-2) The same reaction as in Step (b-1) was carried out that 11 ml (11.0 mmol) of an isopropylmagnesium chloride 1M tetrahydrofuran solution and 2.5 g (10.6 mmol) of 3-bromo-5-chloro-2-methoxy-4-methylpyridine were used, except that 1.25 g (1.1 mmol) of tetrakistriphenylphosphine palladium was used instead of the tetrahydrofuran solution of copper(I) cyanide and lithium chloride, and that 2,3,4-trimethoxy-6-methylbenzoyl chloride prepared from 2.4 g (10.6 mmol) of 2,3,4-trimethoxy-6-methylbenzoic acid and 5 ml of thionyl chloride was dropwise added at 0° C. over a period of 2 hours, followed by stirring at the same temperature for 15 hours to obtain 1.7 g (yield: 43%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine, and the compound was identified by 1HNMR.
Workup
- custom(b-2) The same reaction as in Step (b-1)
- additionwas dropwise added at 0° C. over a period of 2 hours
Sources & evidence
- ORD record
- ord-7517b4632d0249f49bb5dcbfd2d5934c
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653113B2
Reaction notes
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