4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole → 4-(1,4-dioxaspiro[4.5]decan-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

HRID 2047199Notes

Reaction equation

HRID 2047199 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>CCOC(C)=O>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 667335094-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

Product 1

HCID 674943514-(1,4-dioxaspiro[4.5]decan-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazoleYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (505 μmol, 170 mg) was dissolved in 10 mL EtOAc in a 50 mL roundbottom flask. The flask was flushed with argon and 5% palladium on carbon (50 mg) was added. The flask was sealed, degassed under vacuum, and hydrogen gas was added with a balloon. The reaction mixture was stirred at room temperature under hydrogen atmosphere for 18 hours. The reaction was then filtered through celite to yield 4-(1,4-dioxaspiro[4.5]decan-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (165 mg, 487 μmol, 97% yield) as a clear oil.

Workup

  1. customThe flask was flushed with argon and 5% palladium on carbon (50 mg)
  2. additionwas added
  3. customThe flask was sealed
  4. customdegassed under vacuum, and hydrogen gas
  5. additionwas added with a balloon
  6. filtrationThe reaction was then filtered through celite

Sources & evidence

ORD record
ord-acbe557862a84e95b5810a0dfec48227
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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