Spiro[5.5]undec-1-en-3-one → Spiro[5.5]undecan-3-one

HRID 2070537Notes

Reaction equation

HRID 2070537 reaction equation
[CH:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][C:3](=[O:12])[CH:2]=1.[H][H]>O1CCCC1.[C].[Pd]>[CH2:5]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:1][CH2:2][C:3](=[O:12])[CH2:4]1

Participants

5

Reactant 2

HCID 323824Spiro[5.5]undec-1-en-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 574172Spiro[5.5]undecan-3-oneYield 103.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of spiro[5.5]undec-1-en-3-one (8.9 g) obtained in Step 1 in tetrahydrofuran (360 mL) was added 5% palladium carbon (0.89 g), followed by stirring the reaction mixture at room temperature in an atmosphere of hydrogen under normal pressure for 2 hours. Then, the reaction mixture was filtered through Celite and the filtrate was concentrated to obtain spiro[5.5]undecan-3-one (9.3 g).

Workup

  1. filtrationThen, the reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ec93a4c97a2141b8bb175439e7ea48d6
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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