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

HRID 542698Notes

Reaction equation

HRID 542698 reaction equation
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]

Participants

5

Reactant 3

HCID 135483704-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanoneHCID 178444392HCID 178444392, compoundHCID 178444488HCID 178444488, compound

Product 1

HCID 178444407HCID 178444407, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-d8550308f1de45729c13a65157713ce5
Source dataset
uspto-grants-1987_04
Patent number
US04659502

Reaction notes

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