Oxalic acid dihydrate → [Rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester

HRID 1065018ノート

反応式

HRID 1065018 の反応式
O.O.C(O)(=O)C(O)=O.[CH2:9]([O:11][C:12](=[O:37])[CH:13]([O:34][CH2:35][CH3:36])[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22]CC2C=CC=CC=2)=[CH:18][C:17]=1[O:30][CH:31]([CH3:33])[CH3:32])O)[CH3:10]>C(O)(C)C.[Pd]>[CH2:9]([O:11][C:12](=[O:37])[CH:13]([O:34][CH2:35][CH3:36])[CH2:14][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[O:30][CH:31]([CH3:32])[CH3:33])[CH3:10]

参加物

5

反応物 2

HCID 61373Oxalic acid dihydrateHCID 69280524[Rac]-3-(4-benzyloxy-2-isopropoxy-phenyl)-2-ethoxy-3-hydroxy-propionic acid ethyl ester

生成物 1

HCID 69280498[Rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 3776Isopropanol溶媒

実験手順

0.80 g of Pd/C (10%) and 6.0 g of oxalic acid dihydrate were added under argon to 3.20 g (7.95 mmol) of [rac]-3-(4-benzyloxy-2-isopropoxy-phenyl)-2-ethoxy-3-hydroxy-propionic acid ethyl ester [mixture of diastereomers] dissolved in 60 ml of isopropanol. This solution was stirred for 24 hours at room temperature and 50 bar H2. Filtration over dicalite and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9:1 to 1:1) left 0.69 g (29% of theory) of [rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester as yellow oil.

後処理

  1. filtrationFiltration
  2. customover dicalite and evaporation of the solvents
  3. waitleft 0.69 g (29% of theory) of [rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester as yellow oil

出典と根拠

ORDレコード
ord-06db83acd7a84b10accff7ce374ed98e
出典データセット
uspto-grants-2005_11
特許番号
US06969725B2

反応ノート

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