Ethanol → Ethyl 2-oxooctahydropentalene-3a-carboxylate

HRID 547498Notes

Reaction equation

HRID 547498 reaction equation
[O:1]=[C:2]1[CH:9]=[C:8]2[C:4]([C:10]([O:12][CH3:13])=[O:11])([CH2:5][CH2:6][CH2:7]2)[CH2:3]1.[CH2:14](O)C>[Pd]>[O:1]=[C:2]1[CH2:3][C:4]2([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]([CH2:7][CH2:6][CH2:5]2)[CH2:9]1

Participants

4

Reactant 2

HCID 702EthanolHCID 57686983HCID 57686983, compound

Product 1

HCID 10976404Ethyl 2-oxooctahydropentalene-3a-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Methyl 5-oxo-1,2,3,3a,4,5-hexahydropentalene-3a-carboxylate (2.5 g, 12.8 mmol) in ethanol (25 mL) was purged with nitrogen for about 10 minutes with stirring. Palladium on carbon (0.043 g, 20 mol %) was added and the reaction vessel was purged with nitrogen for about 10 minutes. The flow of nitrogen was stopped and the flask was flushed with hydrogen. The reaction mixture was stirred overnight under an atmosphere of hydrogen. The flask was flushed with nitrogen for about 20 minutes. The reaction mixture was passed through a pad of Celite® and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 25% ethyl acetate/heptane) to afford ethyl 2-oxooctahydropentalene-3a-carboxylate (2.04 g, 10.4 mmol, 81%).

Workup

  1. customthe reaction vessel was purged with nitrogen for about 10 minutes
  2. customthe flask was flushed with hydrogen
  3. stirringThe reaction mixture was stirred overnight under an atmosphere of hydrogen
  4. customThe flask was flushed with nitrogen for about 20 minutes
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash column chromatography (eluting with 25% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e7fe4ac3471d449894f4a5ffe8b66b27
Source dataset
uspto-grants-2011_05
Patent number
US07939544B2

Reaction notes

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