Ethyl Acetoacetate → HCID 86740150, compound

HRID 1248090Notes

Reaction equation

HRID 1248090 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][C@H:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.FC(F)(F)C1C=CC(OC2C=CC(O[C@H](C)C(O)=O)=CC=2)=CC=1.C(Cl)(=O)C(Cl)=O.[Na].[C:54]([O:60][CH2:61][CH3:62])(=[O:59])[CH2:55][C:56]([CH3:58])=[O:57]>CCOCC.CN(C=O)C>[C:56]([C@H:55]([C:14](=[O:15])[CH:13]([O:12][C:11]1[CH:18]=[CH:19][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([C:2]([F:23])([F:22])[F:1])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1)[CH3:17])[C:54]([O:60][CH2:61][CH3:62])=[O:59])(=[O:57])[CH3:58]

Participants

8

Reactant 5

HCID 8868Ethyl AcetoacetateHCID 65578Oxalyl chlorideHCID 5360545SodiumHCID 12905973HCID 12905973, compoundHCID 12906016(2R)-2-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanoyl chloride

Product 1

HCID 86740150HCID 86740150, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Following the procedure of Example 12, (R)-2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid chloride is prepared from (R)-2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid (1.0 g, 3.06 mmol) and oxalyl chloride (0.6 ml) in ether (10 ml) and DMF (2 drops). The acid chloride is then reacted with the sodium salt of ethyl acetoacetate (0.084 g of sodium and 0.480 g of ethyl acetoacetate) to give ethyl (R)-2-acetyl-4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-oxopentanoate (XVIII; Q1 is CH, Y is hydrogen, Z is trifluoromethyl and R3 is ethyl).

Sources & evidence

ORD record
ord-cbccc972f0b44760bfa9659eebcb3db4
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Reaction notes

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