4-(3,4-Dichlorophenyl)-4-oxobutyric acid → 2(3H)-Furanone, 5-(3,4-dichlorophenyl)dihydro-
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9](C2C=CC=CC=2)[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=C(C(=O)CCC(O)=O)C=CC=1Cl.ClC1C=C(C(O)CCC(O)=O)C=CC=1Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:13][C:12](=[O:14])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Komponenten
Versuchsvorschrift
A novel three-step process for preparing 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid is disclosed, which involves (1) reducing 4-(3,4-dichlorophenyl)-4-ketobutanoic acid to 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid; (2) then converting the intermediate hydroxy acid formed in the first step to 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone, and (3) thereafter reacting the resulting gamma-butyrolactone compound with benzene in a Friedel-Crafts type reaction to form the desired final product. The latter compound is known to be useful as an intermediate leading to cis-(1S)(4S)- -N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine (sertraline), which is known to be a preferred anti-depressant agent in the field of medicinal chemistry. The aforementioned 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone and 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid are both novel compounds.
Quellen und Nachweise
- ORD-Eintrag
- ord-85cc4cab3f1d42ce82dc8c02004fd3d2
- Quelldatensatz
- uspto-grants-1988_10
- Patentnummer
- US04777288
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