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

HRID 1394807Notes

Reaction equation

HRID 1394807 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8f08f14eb9b04a4fbba2e31965e6c37e
Source dataset
uspto-grants-2008_03
Patent number
US07348349B2

Reaction notes

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