Spiro(4.5)dec-6-ene-8-one → Spiro(4.5)decan-8-one

HRID 1665948

Reaction equation

HRID 1665948 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH:7]=[CH:6]2)[CH2:4][CH2:3][CH2:2]1>CC(=O)OCC.[Pd]>[CH2:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 139772Spiro(4.5)dec-6-ene-8-one

Product 1

HCID 14626805Spiro(4.5)decan-8-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of spiro[4.5]dec-6-en-8-one (1.58 g, 10.5 mmol, prepared according to a literature procedure (N. R. Natale, R. O. Hutchins, Org. Prep. Proc. Int. 9 (1977) 103-108)) in EA (12 mL), Pd/C (75 mg, 10% Pd) is added. The mixture is stirred at it under 1 bar of H2 for 90 min before it is filtered over celite. The solvent of the filtrate is evaporated to give spiro[4.5]decan-8-one (1.56 g) as an almost colourless liquid; 1H NMR (CDCl3): δ 2.36 (t, J=7.0 Hz, 4H), 1.75 (t, J=7.0 Hz, 4H), 1.70-1.65 (m, 4H), 1.62-1.50 (m, 4H).

Workup

  1. filtrationis filtered over celite
  2. customThe solvent of the filtrate is evaporated

Sources & evidence

ORD record
ord-22e00a55d052403492f742dfac8a38aa
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Linked notes

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