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

HRID 1250801
ノート
印刷プレビュー

反応式

HRID 1250801 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 21885
2-Dimethylaminopyridine
触媒
HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e338315390d74529a9fdeb31a01793ea
出典データセット
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06340506B1

反応ノート

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