HCID 67388032, compound → HCID 58453206, compound

HRID 1893079Notes

Reaction equation

HRID 1893079 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH2:27][CH2:26][C:21]4([O:25][CH2:24][CH2:23][O:22]4)[CH2:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]>C1(C)C=CC=CC=1.C(O)C.[Pd]>[CH2:1]([CH:4]1[CH2:5][CH2:6][CH:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]3[CH2:19][CH2:20][C:21]4([O:22][CH2:23][CH2:24][O:25]4)[CH2:26][CH2:27]3)=[CH:16][CH:17]=2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

5

Reactant 1

HCID 67388032HCID 67388032, compound

Product 1

HCID 58453206HCID 58453206, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

The 8-{4-[(E)-2-(4-propylcyclohexyl)ethenyl]phenyl}-1,4-dioxaspiro[4.5]dec-7-en (6.1 g, 16.64 mmol) was dissolved in a mixture of toluene and ethanol (toluene:EtOH=1:3). Pd/C (0.14 g) was added to 200 mL of the resulting solution and hydrogenated for 4 days. After reaction, Pd/C was removed by filtration, and the residue was purified column chromatography (hexane:ether=8:1) to obtain 8-{4-[2-(4-propylcyclohexyl)ethyl]phenyl}-1,4-dioxaspiro[4.5]decane (4.40 g, 72%).

Workup

  1. customwas removed by filtration
  2. customthe residue was purified column chromatography (hexane:ether=8:1)

Sources & evidence

ORD record
ord-1dac311698ff4e389b202dce7ae37b33
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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