8-[(4-Fluorophenyl)methylene]-1,4-dioxaspiro[4.5]decane → 8-[(4-Fluorophenyl)methyl]-1,4-dioxaspiro[4.5]decane

HRID 397163Notes

Reaction equation

HRID 397163 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[H][H]>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:18][CH2:17][C:12]3([O:13][CH2:14][CH2:15][O:16]3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 121339508-[(4-Fluorophenyl)methylene]-1,4-dioxaspiro[4.5]decaneHCID 178418361HCID 178418361, compound

Product 1

HCID 121339518-[(4-Fluorophenyl)methyl]-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring degassed solution of 8-[(4-fluorophenyl)methylene]-1,4-dioxaspiro[4.5]decane (18. 9 g, 76 mmol) and 10% palladium on carbon (3.8 g, Aldrich) in 500 mL of ethyl acetate was added 40 psi of hydrogen gas. The reaction was stirred for 2.5 h and then filtered through a pad of silica gel. The silica gel was washed with ethyl acetate (300 mL). The organic layers were combined and conc in vacuo to a colorless oil yielding 18.0 g. MS (ESI) 253 (M+H).

Workup

  1. filtrationfiltered through a pad of silica gel
  2. washThe silica gel was washed with ethyl acetate (300 mL)
  3. customyielding 18.0 g

Sources & evidence

ORD record
ord-0aff387c627e4b14941cb128ab782c2f
Source dataset
uspto-grants-2003_08
Patent number
US06608227B1

Reaction notes

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