3-Methyl-4-allyloxy-7-(2-thienoyl)benzofuran → 3-Methyl-4-hydroxy-5-propyl-7-(2-thienoyl)benzofuran

HRID 1084860Notes

Reaction equation

HRID 1084860 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:21])=[C:8]([CH2:18][CH:19]=[CH2:20])[CH:9]=[C:10]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])[C:5]=2[O:4][CH:3]=1.CC1C2C(OCC=C)=CC=C(C(C3SC=CC=3)=O)C=2OC=1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[C:6]2[C:7]([OH:21])=[C:8]([CH2:18][CH2:19][CH3:20])[CH:9]=[C:10]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])[C:5]=2[O:4][CH:3]=1

Participants

6

Reactant 3

HCID 151240043-Methyl-4-allyloxy-7-(2-thienoyl)benzofuranHCID 151240053-Methyl-4-hydroxy-5-(2-propen-1-yl)-7-(2-thienoyl)benzofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 151240063-Methyl-4-hydroxy-5-propyl-7-(2-thienoyl)benzofuran

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-methyl-4-hydroxy-5-(2-propen-1-yl)-7-(2-thienoyl)benzofuran, compound 4 (0.228 g, 0.76 mmol) and 5% Pd/C (0.020 g) in absolute ethanol (5 mL) was hydrogenated at 3 atmospheres pressure. After 0.5 hours the requisite amount of hydrogen had been taken up. The catalyst was removed by filtration through celite and the filtrate concentrated to an oil that slowly solidified. Recrystallization of this material from ether/hexane afforded pure 3-methyl-4-hydroxy-5-propyl-7-(2-thienoyl)benzofuran, compound 5 as an off white solid. 1H NMR d 0.98 (3H, t, J=8 Hz), 1.67 (2H, m), 2.40 (3H, s), 2.64 (2H, t, J=6 Hz), 7.14 (1H, m), 7.30 (1H, s), 7.48 (1H, s), 7.63 (1H, d, J=4 Hz), 7.68 (1H, d, J= 4 Hz).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate concentrated to an oil that
  3. customRecrystallization of this material from ether/hexane afforded pure 3-methyl-4-hydroxy-5-propyl-7-(2-thienoyl)benzofuran, compound 5 as an off white solid

Sources & evidence

ORD record
ord-49954b6af0e245df94f6cae6ffde0a20
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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