Piperidine → Ethyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(3-pyridyl)propenoate

HRID 1252479

反応式

HRID 1252479 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:19]=1.N1CCCCC1>C(O)C>[C:14]([C:11]1[CH:10]=[C:7]([CH:8]=[C:24]([C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]=1[OH:13])([CH3:17])([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 96490Ethyl 3-pyridylacetate

生成物 1

HCID 54533232Ethyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(3-pyridyl)propenoate収率 46.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Here, 3,5-di-t-butyl-4-hydroxybenzaldehyde (223 g, 0.952 mol), Ethyl 3-pyridylacetate (157.2 g, 0.952 mol), piperidine (81 g, 0.952 mol) and p-tolunesulfonic acid (0.5 g) are combined in ethanol (2,400 ml) and heated at reflux for 48 hours. The reaction mixture is allowed to cool to room temperature and then stirred on an ice bath, whereupon the product begins to crystallize. The mixture is stored in the freezer overnight, filtered and rinsed with cold ethanol-water (1:1). The product is dried, giving ethyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(3-pyridyl)propenoate (169.1 g) Mp 119.5°-120.5° C.

後処理

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. customto crystallize
  4. customis stored in the freezer overnight
  5. filtrationfiltered
  6. washrinsed with cold ethanol-water (1:1)
  7. customThe product is dried

出典と根拠

ORDレコード
ord-10069ad1bd3e4bc2815288b9b7c98c71
出典データセット
uspto-grants-1988_05
特許番号
US04743606

関連ノート

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