Acetic Acid → Ethyl 3-(5-hydroxy-2-methoxyphenyl)-3-(5-methylthiazol-2-yl)propanoate

HRID 1496984Notes

Reaction equation

HRID 1496984 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:28][CH3:29])=[C:13](/[C:15](/[C:22]2[S:23][C:24]([CH3:27])=[CH:25][N:26]=2)=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=1)C1C=CC=CC=1.CC(O)=O.O>CCO.C1COCC1.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:28][CH3:29])=[C:13]([CH:15]([C:22]2[S:23][C:24]([CH3:27])=[CH:25][N:26]=2)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 117620109(Z)-ethyl 3-(5-(benzyloxy)-2-methoxyphenyl)-3-(5-methylthiazol-2-yl)acrylate

Product 1

HCID 117600036Ethyl 3-(5-hydroxy-2-methoxyphenyl)-3-(5-methylthiazol-2-yl)propanoateYield 60.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (Z)-ethyl 3-(5-(benzyloxy)-2-methoxyphenyl)-3-(5-methylthiazol-2-yl)acrylate (4.0 g, 9.8 mmol), HOAc (2.0 mL), and H2O (5.0 mL) in EtOH (100 mL) and THF (60 mL) was added Pd/C (10%, dry, 5.0 g) under nitrogen atmosphere. The mixture was stirred at room temperature under H2 atmosphere for 48 hrs. After filtration through a pad of Celite and evaporation of the solvent, the residue was purified by silica gel chromatography eluting with petroleum ether/EtOAc (3:1) to afford ethyl 3-(5-hydroxy-2-methoxyphenyl)-3-(5-methylthiazol-2-yl)propanoate (1.9 g, 60%) as a yellow-green gel.

Workup

  1. filtrationAfter filtration
  2. customthrough a pad of Celite and evaporation of the solvent
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with petroleum ether/EtOAc (3:1)

Sources & evidence

ORD record
ord-c64f71bd308b404989843358c8b03b97
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

Loading…