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 1454781Notes

Reaction equation

HRID 1454781 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-3d308a199c704dcea720d8eefd6cd42c
Source dataset
uspto-grants-2009_01
Patent number
US07482336B2

Reaction notes

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