183324-68-7 → HCID 22068554, compound

HRID 906091Notes

Reaction equation

HRID 906091 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].[H][H]>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 57748447183324-68-7HCID 178418361HCID 178418361, compound

Product 1

HCID 22068554HCID 22068554, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

7-Methyl-1-benzofuran-6-carboxylic acid (synthesized in reagent preparation 15) (0.050 g, 0.28 mmol) was solubilized in anhydrous ethanol (2.0 mL) and 0.050 g of palladium (II) hydroxide (20%) was added. This mixture was shaken for 3 hours under 35 psi hydrogen gas using a Parr hydrogenator apparatus. The mixture was filtered through celite and concentrated in vacuo to give crude 7-methyl-2,3-dihydro-1-benzofuran-6-carboxylic acid (0.049 g, 97% yield) which was used without further purification. 1H NMR (400 MHz, d6-DMSO): 12.67 (broad s, 1H), 7.33 (d, 1H), 7.11 (d, 1H), 4.55 (t, 2H), 3.23 (t, 2H), 2.32 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c06d9d954aec4f8da1f5bc85591a3e3d
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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