4-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanone → HCID 178444407, Verbindung

HRID 542698

Reaktionsgleichung

Reaktionsgleichung von HRID 542698
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C([C@H]1CC[C@H](CC(Cl)=O)CC1)CCCC.CC1(C)CO[C:39]([CH:42]2[CH2:47][CH2:46][C:45](=O)[CH2:44][CH2:43]2)=[N:38]1>C1C=CC=CC=1>[C:39]([C@H:42]1[CH2:47][CH2:46][C@H:45]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@H:10]3[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][CH2:11]3)=[CH:4][CH:3]=2)[CH2:44][CH2:43]1)#[N:38]

Komponenten

5

Edukt 3

HCID 135483704-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanoneHCID 178444392HCID 178444392, VerbindungHCID 178444488HCID 178444488, Verbindung

Produkt 1

HCID 178444407HCID 178444407, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

1-(p-Bromophenyl)-2-(trans-4-n-pentylcyclohexyl)-ethane [obtainable by Friedel-Crafts acylation of benzene with trans-4-n-pentylcyclohexylacetyl chloride, Wolff-Kishner reduction of the carbonyl group and bromination of the aromatic in the p-position] is subjected to a Grignard reaction with 4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanone. Detachment of water, with simultaneous removal of the oxazolyl protective group, by boiling with ethanolic H2SO4, hydrogenation of the double bond, conversion of the ethyl ester into the amide, dehydration analogously to Example 2 and customary working up gives 1-[p-(trans-4-cyanocyclohexyl)-phenyl]-2-(trans-4-n-pentylcyclohexyl)-ethane.

Aufarbeitung

  1. customDetachment of water, with simultaneous removal of the oxazolyl protective group

Quellen und Nachweise

ORD-Eintrag
ord-d8550308f1de45729c13a65157713ce5
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659502

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