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

HRID 2240819Notes

Reaction equation

HRID 2240819 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH:5]=[CH: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]([C:29]([F:32])([F:31])[F: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[CH2:33][CH3:34])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:35])[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]([C:29]([F:30])([F:31])[F:32])=[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[CH2:33][CH3:34])[CH3:2]

Participants

4

Reactant 1

HCID 671883473-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester

Product 1

HCID 575089143-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester (630 mg, 1.25 mmol) in ethanol (25 mL), a suspension of Pd/C (400 mg, 10% Pd) in ethanol (15 mL) is added and the resulting slurry is stirred at 65° C. for 16 h under 8 bar of H2. The catalyst is filtered off and the solvent of the filtrate is evaporated. The residue is separated by CC on silica gel eluting with heptane:EA 4:1 to give 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester (340 mg, contains traces of the corresponding isopropyl ester) as a colourless oil; LC-MS: tR=1.28 min, [M+1]=509.49.

Workup

  1. additionis added
  2. filtrationThe catalyst is filtered off
  3. customthe solvent of the filtrate is evaporated
  4. customThe residue is separated by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-372fe1c3ba7149f39aaac5eef14c4265
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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