Methyl(6-hydroxy-4-vinyl-1-benzothiophen-3-yl)acetate → Methyl(6-hydroxy-4-ethyl-1-benzothiophen-3-yl)acetate

HRID 591508Notes

Reaction equation

HRID 591508 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:9]2[C:10]([CH:15]=[CH2:16])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1>[Pd].CCOC(C)=O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:9]2[C:10]([CH2:15][CH3:16])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

4

Reactant 1

HCID 89767599Methyl(6-hydroxy-4-vinyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 131734524Methyl(6-hydroxy-4-ethyl-1-benzothiophen-3-yl)acetateYield 38.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl(6-hydroxy-4-vinyl-1-benzothiophen-3-yl)acetate (230 mg), 10% Pd—C (50% wet, 99 mg) and EtOAc (5 mL) was hydrogenated under balloon pressure at room temperature overnight. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (89 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-2629055e283648e5be52e1e6536ecfbd
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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