4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine → 4-(4-Pyridyl)cyclohexanone ethylene ketal

HRID 1193341Notes

Reaction equation

HRID 1193341 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>CO>[O:1]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=3)[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 137720544-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine

Product 1

HCID 578925724-(4-Pyridyl)cyclohexanone ethylene ketalYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine (3.5 g, 16.1 mmol, 1 eq) was dissolved in MeOH (80 ml) and degassed for 15 min with argon. Pd(OH)2 (1.75 g, 50%) was added, and hydrogenation was carried out for 3 h at RT under balloon pressure (H2). After monitoring by thin-layer chromatography, the reaction mixture was filtered off over Celite and the filtrate was concentrated under reduced pressure. Yield: 84% (3.0 g, 13.6 mmol).

Workup

  1. customdegassed for 15 min with argon
  2. additionPd(OH)2 (1.75 g, 50%) was added
  3. filtrationthe reaction mixture was filtered off over Celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0b127053b7346abb255382f7a54abd8
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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