3-{2-Ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-6-methyl-phenyl}-propionic acid ethyl ester → 3-{2-Ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-6-methyl-phenyl}-propionic acid ethyl ester

HRID 1013446Notes

Reaction equation

HRID 1013446 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH:14]=[CH:15][C:16]([C:18]2[S:19][C:20]([CH2:29][CH3:30])=[C:21]3[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][C:22]=23)=[O:17])=[CH:9][C:8]=1[CH2:31][CH3:32])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([CH2:29][CH3:30])=[C:21]3[CH2:26][C:25]([CH3:27])([CH3:28])[CH2:24][CH2:23][C:22]=23)=[O:17])=[CH:9][C:8]=1[CH2:31][CH3:32])[CH3:2]

Participants

4

Reactant 1

HCID 673160223-{2-Ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-6-methyl-phenyl}-propionic acid ethyl ester

Product 1

HCID 673164263-{2-Ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-6-methyl-phenyl}-propionic acid ethyl esterYield 61.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-{2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-6-methyl-phenyl}-propionic acid ethyl ester (153 mg, 0.328 mmol) in ethanol, Pd/C (80 mg, 10% Pd, moistened with 50% water) is added and the resulting slurry is stirred at rt for 72 h under 1 bar of H2. The reaction mixture is filtered and the filtrate is evaporated. The crude product is purified by prep. HPLC (Grom-Sil 120 ODS-4-HE, 30×75 mm, 10 μm, acetonitrile/water (0.5% HCOOH), 20% to 95% acetonitrile) to give 3-{2-ethyl-4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-6-methyl-phenyl}-propionic acid ethyl ester (95 mg) as an amorphous solid; LC-MS: tR=1.26 min, [M+1]=469.40.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-beeb292b9f024d2087e1575ffe02f9f9
Source dataset
uspto-grants-2011_07
Patent number
US07981924B2

Reaction notes

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