Acetic Acid → HCID 18625569, compound

HRID 1859409Notes

Reaction equation

HRID 1859409 reaction equation
C([O:8][CH:9]([CH:14]([CH:16]1[CH2:18][CH2:17]1)[CH3:15])[C:10]([O:12][CH3:13])=[O:11])C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[OH:8][CH:9]([CH:14]([CH:16]1[CH2:18][CH2:17]1)[CH3:15])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18625556HCID 18625556, compound

Product 1

HCID 18625569HCID 18625569, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-benzyloxy-3-cyclopropylbutanoate (1.0 g, 4.0 mmol) and acetic acid (1 mL) in MeOH (25 mL) was added 10% palladium on charcoal (100 mg). Hydrogen gas was bubbled though the stirred solution for several minutes, and the reaction mixture was stirred under an atmosphere of hydrogen for 6 h. Nitrogen gas was bubbled through the solution to purge all of the hydrogen and the catalyst was removed by filtration. The filtrate solvents were removed under reduced pressure and the residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was separated, dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give methyl 2-hydroxy-3-cyclopropylbutanoate as a colorless oil. HPLC RT=2.47 min (Method A); LC-MS m/z=159; 1H NMR 400 MHz, CDCl3, 4.25 ppm (dd, J=3.3, 6.5 Hz, 1H), 3.77 ppm (s, 3H), 2.72 ppm (d, J=6.6 Hz, 1H), 1.05 ppm (m, 1h) 0.95 ppm (d, J=7 Hz, 3H), 0.84 ppm (m, 1H), 0.50 ppm (m, 2H), 0.19 ppm (m, 1H), 0.10 ppm (m, 1H)

Workup

  1. customHydrogen gas was bubbled though the stirred solution for several minutes
  2. customNitrogen gas was bubbled through the solution
  3. customto purge all of the hydrogen
  4. customthe catalyst was removed by filtration
  5. customThe filtrate solvents were removed under reduced pressure
  6. customthe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b59ba70caa114ef198f4a34066e029bc
Source dataset
uspto-grants-2003_03
Patent number
US06528503B2

Reaction notes

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