4-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanone → HCID 178444407、化合物

HRID 542698ノート

反応式

HRID 542698 の反応式
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]

参加物

5

反応物 3

HCID 135483704-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanoneHCID 178444392HCID 178444392、化合物HCID 178444488HCID 178444488、化合物

生成物 1

HCID 178444407HCID 178444407、化合物

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d8550308f1de45729c13a65157713ce5
出典データセット
uspto-grants-1987_04
特許番号
US04659502

反応ノート

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