8-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene → 8-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]decane

HRID 1095244Notes

Reaction equation

HRID 1095244 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[H][H]>C1(C)C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][CH2:16][C:11]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 187879328-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-eneHCID 178418361HCID 178418361, compound

Product 1

HCID 187879268-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

The compound (17) was dissolved in a mixed solvent of toluene (150 ml) and Solmix (150 ml) and 3.48 g of Pd/C was added thereto. The mixture was stirred at room temperature under a hydrogen atmosphere until hydrogen absorption had ceased. After the reaction had been completed, Pd/C was removed and then the solvent was distilled off. The residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=9:1 by volume) as an eluent and silica gel as a stationary phase powder and dried, giving 61.9 g of 8-(3-fluorophenyl)-1,4-dioxaspiro[4,5]decane (18). The yield based on the compound (17) was 88.1%.

Workup

  1. additionwas added
  2. customPd/C was removed
  3. distillationthe solvent was distilled off
  4. customThe residue was purified with a fractional operation by means of column chromatography
  5. customsilica gel as a stationary phase powder and dried

Sources & evidence

ORD record
ord-54864268b135497891ac8bf95a3dc1be
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

Loading…