Ethanol → Ethyl 2-oxooctahydropentalene-3a-carboxylate

HRID 1908211Notes

Reaction equation

HRID 1908211 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-47dc8ff9131a4235b9c2f946dbca2ce0
Source dataset
uspto-grants-2013_12
Patent number
US08598199B2

Reaction notes

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