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 602937Notes

Reaction equation

HRID 602937 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-022b8f1566d547fb8d88fdae0bcb18d5
Source dataset
uspto-grants-2011_03
Patent number
US07906649B2

Reaction notes

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