Ethyl (2E)-3-(4-hydroxy-1-benzothiophen-7-yl)prop-2-enoate → Ethyl 3-(4-hydroxy-1-benzothiophen-7-yl)propanoate

HRID 2177201Notes

Reaction equation

HRID 2177201 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1>[C].[Pd].C(O)C>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 90442051Ethyl (2E)-3-(4-hydroxy-1-benzothiophen-7-yl)prop-2-enoate

Product 1

HCID 90418184Ethyl 3-(4-hydroxy-1-benzothiophen-7-yl)propanoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of H2, was placed ethyl (2E)-3-(4-hydroxy-1-benzothiophen-7-yl)prop-2-enoate (200 mg, 0.68 mmol, 1.00 equiv, 85%), Palladium carbon (100 mg), ethanol (4 mL). The resulting solution was stirred overnight at 25° C. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was purified by thin layer chromatography developed with ethyl acetate/petroleum ether (1:5). This resulted in 150 mg (79%) of ethyl 3-(4-hydroxy-1-benzothiophen-7-yl)propanoate as colorless oil.

Workup

  1. customInto a 100-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of H2
  3. filtrationThe solids were filtered out
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThe residue was purified by thin layer chromatography
  6. customThis resulted in 150 mg (79%) of ethyl 3-(4-hydroxy-1-benzothiophen-7-yl)propanoate as colorless oil

Sources & evidence

ORD record
ord-98f6e44141fa4d5d86b63fa6c4d5f9d3
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…