Potassium Carbonate → 8-{4-[2-Fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-cyclohexyl}-1,4-dioxa-spiro[4,5]decane

HRID 1095237Notes

Reaction equation

HRID 1095237 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[C:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:34][CH2:33][C:28]3([O:32][CH2:31][CH2:30][O:29]3)[CH2:27][CH2:26]2)[CH2:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[H][H]>C1(C)C=CC=CC=1.C(O)(C)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1[CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:34][CH2:33][C:28]3([O:29][CH2:30][CH2:31][O:32]3)[CH2:27][CH2:26]2)[CH2:21][CH2:20]1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 582122828-{4-[2-Fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-cyclohex-3-enyl}-1,4-dioxa-spiro[4,5] decaneHCID 178418361HCID 178418361, compound

Product 1

HCID 582122948-{4-[2-Fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-cyclohexyl}-1,4-dioxa-spiro[4,5]decane

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalyst2×HCID 1140TolueneSolventHCID 3776IsopropanolSolventHCID 23938PalladiumSolvent

Procedure

The compound (4) was dissolved in a mixed solvent of toluene (150 ml) and isopropyl alcohol (100 ml), and palladium on carbon catalyst (NX type of 5% Pd/C; 50% wet; made by N. E. Chemcat; hereinafter referred to as Pd/C) (3.06 g) and potassium carbonate (0.52 g) were 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, and 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 further purified by means of recrystallization from heptane and dried, giving 26.35 g of 8-{4-[2-fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-cyclohexyl}-1,4-dioxa-spiro[4,5]decane (5). The yield based on the compound (4) was 44.6%.

Workup

  1. additionwere 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 further purified by means of recrystallization from heptane
  6. customdried

Sources & evidence

ORD record
ord-a546018c421241ea9d99a1558bed350a
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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