Potassium Hydroxide → (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester

HRID 885893ノート

反応式

HRID 885893 の反応式
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[C:12]([O:16][C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][N:21]=1)([CH3:15])([CH3:14])[CH3:13].[OH-].[K+]>CCO>[C:12]([O:16][C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:10]/[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)=[O:11])=[CH:22][N:21]=1)([CH3:15])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 5852641-(4-(Hydroxymethyl)phenyl)ethanoneHCID 44819897tert-Butyl (E)-3-(5-formyl-pyridin-2-yl)-acrylate

生成物 1

HCID 67049926(E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester収率 34.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 1-(4-hydroxymethyl-phenyl)-ethanone (750 mg, 5 mmol) in EtOH (15 ml) was added dropwise at 0° C. to a stirred solution of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (described in Example 11 STEP A-D, 1.16 g, 5 mmol) and 1.7 M KOH (4.4 ml) in EtOH (10 ml). The mixture was stirred at 0° C. for 5 h and the resulting precipitate was filtered and triturated with di-isopropylether to give 630 mg of desired (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester. The mother liquors were diluted with water and extracted with AcOEt. The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was triturated with EtOH to give additional 70 mg of (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester.

後処理

  1. filtrationthe resulting precipitate was filtered
  2. customtriturated with di-isopropylether

出典と根拠

ORDレコード
ord-affe6ed0ebbf401793d5aac7c4011cce
出典データセット
uspto-grants-2012_08
特許番号
US08242175B2

反応ノート

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