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Pyridine → 3,5-Dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester

HRID 1250801
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HRID 1250801 반응식
[CH3:1][O:2][C:3](=[O:22])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[C:8]([O:20][CH3:21])[CH:7]=1.[N+:23]([C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([N+:35]([O-:37])=[O:36])[CH:34]=1)[C:29](Cl)=[O:30])([O-:25])=[O:24].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CC=CN=1)C>[C:3]([O-:22])(=[O:2])[CH3:4].[CH3:21][O:20][C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([O:2][CH3:1])=[O:22])[CH:11]=[CH:10][C:9]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:29](=[O:30])[C:28]1[CH:27]=[C:26]([N+:23]([O-:25])=[O:24])[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 1049PyridineHCID 74323,5-Dinitrobenzoyl chlorideHCID 541470624-(6-Hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester

생성물 2

HCID 175AcetateHCID 543196263,5-Dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester수율 176.7%

시약·촉매·용매 2

HCID 21885
2-Dimethylaminopyridine
촉매
HCID 6344Dichloromethane용매

실험 절차

2.50 g (8.11 mmol) of 4-(6-hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester, 1.96 g (8.51 mmol) of 3,5-dinitrobenzoyl chloride and 10 mg (0.08 mmol) of dimethylaminopyridine were dissolved in 25 ml of methylene chloride. 3.3 ml (40.5 mmol) of pyridine were added dropwise, in the course of 20 minutes at 0° C., to the resulting clear solution. After 2 hours at 0° C. the reaction mixture was partitioned between methylene chloride and water; the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water. The organic phase was then dried over magnesium sulphate, filtered and concentrated by evaporation. Chromatography of the residue on 150 g of silica gel using toluenelethyl acetate 9:1 yielded 3.6 g of 3,5-dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester.

후처리

  1. customAfter 2 hours at 0° C. the reaction mixture was partitioned between methylene chloride and water
  2. washthe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water
  3. dry with materialThe organic phase was then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-e338315390d74529a9fdeb31a01793ea
출처 데이터셋
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06340506B1

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