4-Chloro-3-hydroxybenzaldehyde → Ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate

HRID 1639889ノート

反応式

HRID 1639889 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1/[CH:11]=[CH:12]/[CH:13]=[C:14](/[N:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)\[C:15]([O:17][CH2:18][CH3:19])=[O:16].[Cl:40][C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][C:42]=1[OH:49]>C(#N)C>[Cl:40][C:41]1[CH:48]=[CH:47][C:44]([C:45]2[N:20]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:12][C:11]=2[C:4]2[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:43][C:42]=1[OH:49]

参加物

4

反応物 2

HCID 138651144-Chloro-3-hydroxybenzaldehydeHCID 86637360ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoate

生成物 1

HCID 66720714Ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate収率 41.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Reflux a solution of 7.54 g (14 mmol) of ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoate and 2.42 g (15.4 mmol) of 4-chloro-3-hydroxybenzaldehyde in 280 mL of anhydrous acetonitrile for 96 h. After cooling to RT, concentrate the reaction mixture under reduced pressure and purify the residue obtained by silica gel column chromatography, eluting with a cyclohexane/ethyl acetate (EtOAc) gradient from 0 to 30% of EtOAc. After concentration under reduced pressure, we obtain 2.4 g of ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate in the form of white powder.

後処理

  1. concentrationconcentrate the reaction mixture under reduced pressure
  2. custompurify the residue
  3. customobtained by silica gel column chromatography
  4. washeluting with a cyclohexane/ethyl acetate (EtOAc) gradient from 0 to 30% of EtOAc
  5. concentrationAfter concentration under reduced pressure, we

出典と根拠

ORDレコード
ord-0d06db0c8d324b92927a969ba8431a75
出典データセット
uspto-grants-2012_02
特許番号
US08110579B2

反応ノート

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