4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one → 4-Triethylsiloxy-4-trifluoromethylcyclohexanone

HRID 231330Notes

Reaction equation

HRID 231330 reaction equation
[CH2:1]([Si:3]([CH2:18][CH3:19])([CH2:16][CH3:17])[O:4][C:5]1([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:9][C:8](=[O:11])[CH:7]=[CH:6]1)[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:16]([Si:3]([CH2:1][CH3:2])([CH2:18][CH3:19])[O:4][C:5]1([C:12]([F:14])([F:13])[F:15])[CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH2:10]1)[CH3:17]

Participants

5

Reactant 2

HCID 143434944-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 200620264-Triethylsiloxy-4-trifluoromethylcyclohexanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 291 mg of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one in 2 mL of absolute ethanol was treated with a few mg of 5% palladium on carbon, hydrogenated in a Parr shaker for one hour under 50 psig of hydrogen, and filtered. Concentration of the filtrate gave 4-triethylsiloxy-4-trifluoromethylcyclohexanone: 1H NMR (CDCl3) δ 0.45-1.16 (m, 15H), 1.92-2.89 (m, 8H); mass spectrum (70 eV) m/z (relative intensity) 267 (19, M-C2H5), 115 (45), 105 (33), 87 (100), 81 (22), 77 (67), 73 (20), 67 (29), 59 (57), 55 (84), 47 (20).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-60a1d9e7b000496ba5af8df16e7fe996
Source dataset
uspto-grants-1989_07
Patent number
US04845258

Reaction notes

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