Ethyl Acetoacetate → HCID 86740148, compound

HRID 1248089Notes

Reaction equation

[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:21]=[CH:20][C:13]([O:14][C@H:15]([CH3:19])[C:16](Cl)=[O:17])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.FC(F)(F)C1C=CC(OC2C=CC(O[C@H](C)C(O)=O)=CC=2)=NC=1.S(Cl)(Cl)=O.[Na].[C:52]([O:58][CH2:59][CH3:60])(=[O:57])[CH2:53][C:54]([CH3:56])=[O:55]>>[C:54]([C@H:53]([C:16](=[O:17])[CH:15]([O:14][C:13]1[CH:20]=[CH:21][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:23])([F:22])[F:1])=[CH:8][N:7]=2)=[CH:11][CH:12]=1)[CH3:19])[C:52]([O:58][CH2:59][CH3:60])=[O:57])(=[O:55])[CH3:56]

Participants

Reactant 5

HCID 8868Ethyl Acetoacetate

HCID 24386Thionyl Chloride

HCID 91733Fluazifop-P

HCID 5360545Sodium

HCID 13055221HCID 13055221, compound

Product 1

HCID 86740148HCID 86740148, compound

Procedure

Following the above procedures, (R)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid chloride, prepared from (R)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid and thionyl chloride, is reacted with the sodium salt of ethyl acetoacetate to give ethyl (R)-2-acetyl-4-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]-3-oxopentanoate (XVIII: Q1 is N, Y is hydrogen, Z is trifluoromethyl and R3 is ethyl). This pentanoate is then heated with sodium chloride to give (R)-5-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]2,4-hexanedione (XIX; Q1 is N, Y is hydrogen and Z is trifluoromethyl).

Sources & evidence

ORD record: ord-bd398e64570343ba90febfa69bbbd91d
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04522647

Reaction notes

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