3-(3-Hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-acrylic acid ethyl ester → 3-(3-Hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-propionic acid ethyl ester

HRID 1158944ノート

反応式

HRID 1158944 の反応式
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[C:9]([CH3:15])[C:8]=1[OH:16])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[C:9]([CH3:15])[C:8]=1[OH:16])[CH3:2]

参加物

4

反応物 1

HCID 543009153-(3-Hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-acrylic acid ethyl ester

生成物 1

HCID 586367193-(3-Hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-propionic acid ethyl ester収率 72.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

The 3-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-acrylic acid ethyl ester (34) (15.2 g, 64 mmol) in ethyl acetate (250 mL) was hydrogenated in the presence of 10% palladium on carbon (8.0 g) at room temperature overnight. The product was filtered through a celite pad and evaporated. The crude product thus obtained was purified by column chromatography on silica gel using a gradient mixture of ethyl acetate:hexane:methyl alcohol (7:7:1 to 4:4:1) to give 3-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-propionic acid ethyl ester (35) (11.1 g, 62% yield) as a colorless solid.

後処理

  1. filtrationThe product was filtered through a celite pad
  2. customevaporated
  3. customThe crude product thus obtained
  4. customwas purified by column chromatography on silica gel using
  5. additiona gradient mixture of ethyl acetate:hexane:methyl alcohol (7:7:1 to 4:4:1)

出典と根拠

ORDレコード
ord-8f9aa6eda0c04b8fbc5fece974f28cbc
出典データセット
uspto-grants-2010_10
特許番号
US07812037B2

反応ノート

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