Methyl acetoacetate → HCID 20278413, compound

HRID 1248086Notes

Reaction equation

HRID 1248086 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([O:13][C:14]1[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20](Cl)=[O:21])=[CH:16][CH:15]=1)[CH:7]=[N:6]2.[C:28]([CH:31](C(=O)C(OC1C=CC(OC2C=NC3C(=CC=C(F)C=3)N=2)=CC=1)C)[C:32]([O:34][CH3:35])=[O:33])(=[O:30])[CH3:29].C(Cl)(=O)C(Cl)=O.[Na].COC(=O)CC(C)=O>>[C:28]([CH:31]([C:20](=[O:21])[CH:19]([O:18][C:17]1[CH:24]=[CH:25][C:14]([O:13][C:8]2[CH:7]=[N:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:2]([F:27])([F:26])[F:1])[CH:4]=3)[N:9]=2)=[CH:15][CH:16]=1)[CH3:23])[C:32]([O:34][CH3:35])=[O:33])(=[O:30])[CH3:29]

Participants

6

Reactant 5

HCID 7757Methyl acetoacetateHCID 65578Oxalyl chlorideHCID 5360545SodiumHCID 20278422HCID 20278422, compoundHCID 54519821HCID 54519821, compound

Product 1

HCID 20278413HCID 20278413, compound

Procedure

In the same manner, 2-[4-(6-trifluoromethyl-2-quinoxalinyloxy)phenoxy]propionic acid chloride is prepared from the corresponding propionic acid and oxalyl chloride, and is then reacted with the sodium salt of methylacetoacetate to give methyl 2-acetyl-4-[4-(6-trifluoromethyl-2-quinoxalinyloxy)phenoxy]-3-oxopentanoate (XIV; X' is CF3 and X" is hydrogen). The pentanoate is then heated with sodium chloride and DMSO to yield 5-[4-(6-trifluoromethyl-2-quinoxalinyloxy)phenoxy]-2,4-hexanedione (XV; X' is CF3 and X" is hydrogen).

Sources & evidence

ORD record
ord-d2f8ba1b331a49f095ab9c5954d86d23
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Reaction notes

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