HCID 21030126, compound → HCID 21030102, compound

HRID 1829076Notes

Reaction equation

HRID 1829076 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10](=[O:11])[O:9][CH:8]([CH2:12][C:13]([O:15]CCCC)=[O:14])[C:7]=2[CH:20]=1>Cl.O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10](=[O:11])[O:9][CH:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7]=2[CH:20]=1

Participants

4

Reactant 1

HCID 21030126HCID 21030126, compound

Product 1

HCID 21030102HCID 21030102, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21885828Hydrate;hydrochlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of butyl (6-methoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetate (251 mg, 0.902 mmol) in 6M HCl/H2O (10.0 ml) was heated at 80° C. for 2.5 hours. The mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, and rotary evaporated to give a pale yellow solid. The pale yellow solid was triturated at room temperature with 10% EtOAc/Hexane and then only hexane to afford (6-methoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetic acid as a white solid (150.2 mg, 75%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customrotary evaporated
  5. customto give a pale yellow solid
  6. customThe pale yellow solid was triturated at room temperature with 10% EtOAc/Hexane

Sources & evidence

ORD record
ord-aa4beacc895a4a0c9c76fc643197d600
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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