Methyl 3-oxovalerate → Methyl 2-propionyl-4-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-3-oxopentanoate

HRID 1248082Notes

Reaction equation

HRID 1248082 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Na].[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])(=[O:29])[CH2:27][CH3:28]>C1C=CC=CC=1>[C:26]([CH:30]([C:19](=[O:20])[CH:18]([O:17][C:16]1[CH:23]=[CH:24][C:13]([O:12][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=2)=[CH:14][CH:15]=1)[CH3:22])[C:31]([O:33][CH3:34])=[O:32])(=[O:29])[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 121699Methyl 3-oxovalerateHCID 5360545SodiumHCID 13389070HCID 13389070, compound

Product 1

HCID 20278409Methyl 2-propionyl-4-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Following the procedure of Example 4, 2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid chloride is added to the sodium salt of methyl propionylacetate in benzene to give methyl 2-propionyl-4-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-3-oxopentanoate (cpd. 27, Table C). This pentanoate is then heated with sodium chloride and DMSO to give 2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-3,5-heptanedione (cpd. 27, Table D).

Sources & evidence

ORD record
ord-f828e5c886544595a05e1637760a3184
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Reaction notes

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