8-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene → 8-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decane

HRID 2353410Notes

Reaction equation

HRID 2353410 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH:11]=1>CO.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:11][CH2:12][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:18][CH2:19]1

Participants

5

Reactant 1

HCID 574243608-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 574243618-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene in methanol (240 mL) and ethyl acetate (5 mL) was treated with 10% palladium on carbon (7.0 g) and stirred under an atmosphere of hydrogen gas (40 psig) overnight. The reaction mixture was filtered over Celite. The filtrate was concentrated and chromatographed (silica gel, gradient 5-7% ethyl acetate in hexane) to yield the title compound.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. concentrationThe filtrate was concentrated
  3. customchromatographed (silica gel, gradient 5-7% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-88c39279a7a2421d8d5d213637a33bbf
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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