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

HRID 542698노트

반응식

HRID 542698 반응식
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]

참가 물질

5

반응물 3

HCID 135483704-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanoneHCID 178444392HCID 178444392, 화합물HCID 178444488HCID 178444488, 화합물

생성물 1

HCID 178444407HCID 178444407, 화합물

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d8550308f1de45729c13a65157713ce5
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04659502

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