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1-Bromooctane → 5-octyl-2-(4-octyloxyphenyl)pyridine N-oxide

HRID 1780542
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HRID 1780542 반응식
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:28][CH:27]=2)=[N:24][CH:25]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(OC1C=CC([Li])=CC=1)CCCCCCC.BrCCCCCCCC>C(Cl)Cl.N1C=CC=CC=1>[CH2:12]([C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:28][CH:27]=2)=[N+:24]([O-:9])[CH:25]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]
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참가 물질

7

반응물 4

HCID 81401-BromooctaneHCID 70297m-Chloroperbenzoic acidHCID 3126238Pyridine, 5-octyl-2-[4-(octyloxy)phenyl]-HCID 178506738HCID 178506738, 화합물

생성물 1

HCID 543682835-octyl-2-(4-octyloxyphenyl)pyridine N-oxide수율 65.2%

시약·촉매·용매 2

HCID 1049
Pyridine
용매
HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3.03 g (12.3 mmol) of 3-chloroperbenzoic acid in 30 ml of methylene chloride is added dropwise at a temperature of 0° to 5° C. to 3.23 g (8.2 mmol) of 5-octyl-2-(4-octyloxyphenyl)pyridine (prepared, for example, analogously to C. S. Giam, J. Staut, J. Chem. Soc., Chem. Commun. 478 (1970) from pyridine, 4-octyloxyphenyllithium and 1-bromooctane) in 30 ml of methylene chloride. After a reaction time of 3 hours at room temperature, the mixture is washed once with 5% sodium carbonate and twice with sodium chloride solution, the organic phase is dried over sodium sulfate, filtered off, and the solvent is removed by distillation. Purification of the residue by chromatography (silica gel, 8:2 methylene chloride/ethyl acetate) gives 2.20 g of 5-octyl-2-(4-octyloxyphenyl)pyridine N-oxide. ##STR13##

후처리

  1. washAfter a reaction time of 3 hours at room temperature, the mixture is washed once with 5% sodium carbonate and twice with sodium chloride solution
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. filtrationfiltered off
  4. customthe solvent is removed by distillation
  5. customPurification of the residue by chromatography (silica gel, 8:2 methylene chloride/ethyl acetate)

출처 및 근거

ORD 기록
ord-4e58e304ac9a499eb2b7ec70627013d7
출처 데이터셋
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05630962

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