HCID 58535838, compound → HCID 58535363, compound

HRID 1941733Notes

Reaction equation

HRID 1941733 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]3[O:23][CH2:22][CH:21]([CH:24]4[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]4)[CH2:20][CH:19]=3)=[C:12]([F:33])[C:11]=2[F:34])=[C:6]([F:35])[C:5]=1[F:36])[CH3:2]>C1(C)C=CC=CC=1.CC(O)C.[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]3[CH2:19][CH2:20][CH:21]([CH:24]4[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]4)[CH2:22][O:23]3)=[C:12]([F:33])[C:11]=2[F:34])=[C:6]([F:35])[C:5]=1[F:36])[CH3:2]

Participants

5

Reactant 1

HCID 58535838HCID 58535838, compound

Product 1

HCID 58535363HCID 58535363, compoundYield 30.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

6-(2-(4′-Ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)ethyl)-3-(4-propylcyclohexyl)-3,4-dihydro-2H-pyran (31) (2.5 g) prepared in the second step was dissolved in a mixture of toluene (5 ml) and IPA (5 ml), and 5%-Pd/C 125 mg) was added. The stirring was continued under a hydrogen atmosphere at room temperature for 12 hours. 5%-Pd/C was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 20 g, eluent: toluene), and then by recrystallization (heptane/toluene=50/50 by volume) to give 2-(2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)ethyl)-5-(4-propylcyclohexyl)tetrahydro-2H-pyran (32) (0.7 g) in 30.1% yield.

Workup

  1. additionwas added
  2. custom5%-Pd/C was removed by filtration
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (silica gel: 20 g, eluent: toluene)
  5. customby recrystallization (heptane/toluene=50/50 by volume)

Sources & evidence

ORD record
ord-68c869586a464c26b5b5d0d9e6c5f667
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

Loading…