Methanol → HCID 86705339, compound

HRID 587984Notes

Reaction equation

HRID 587984 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:12][C:11](/[CH:13]=[C:14](\[CH2:18][CH3:19])/[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.C(Cl)(Cl)Cl>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6]([C:8]1[S:12][C:11]([CH2:13][CH:14]([CH2:18][CH3:19])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 6212ChloroformHCID 90018946HCID 90018946, compound

Product 1

HCID 86705339HCID 86705339, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

(E)-3-(5-tert-butoxycarbonylthiophen-2-yl)-2-ethylpropenoic acid (20.43 g, 72.4 mmol) was dissolved in ethyl acetate (300 mL), methanol (20 mL) and chloroform (10 mL), palladium hydroxide (2.0 g) was added, and the mixture was stirred at room temperature overnight under a hydrogen atmosphere. After completion of the reaction, palladium hydroxide was removed by celite filtration, and the solvent was evaporated under reduced pressure to give the title compound (20.6 g, quantitative).

Workup

  1. customwas removed by celite filtration
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fa4122911aa04e8cad7b354c57c3db01
Source dataset
uspto-grants-2016_01
Patent number
US09227949B2

Reaction notes

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