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Dichloromethane → 5-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-2-(4-propylcyclohexyl)tetrahydropyran

HRID 1941726
Notes
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Reaction equation

HRID 1941726 reaction equation
ClCCl.[CH2:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][CH:22]([CH:25]4[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:26]4)[O:21][CH:20]3O)=[C:15]([F:35])[C:14]=2[F:36])=[C:9]([F:37])[C:8]=1[F:38])[CH3:5].C([SiH](CC)CC)C>O>[CH2:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:20][O:21][CH:22]([CH:25]4[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:26]4)[CH2:23][CH2:24]3)=[C:15]([F:35])[C:14]=2[F:36])=[C:9]([F:37])[C:8]=1[F:38])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12052TriethylsilaneHCID 585356523-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol

Product 1

HCID 585352905-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-2-(4-propylcyclohexyl)tetrahydropyranYield 36.1%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Dichloromethane (30 ml) was added to 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol (12) (2.29 g) prepared in the tenth step. Triethylsilane (1.93 g) and a boron trifluoride-diethyl ether complex (2.37 g) were added dropwise to the solution at −30° C. After 3 hours of stirring, water (30 ml) was added to give two layers. The organic layer was washed with water, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 200 g, eluent: heptane/ethyl acetate=80/20 by volume) and then by recrystallization (heptane/ethyl acetate=90/10 by volume) to give 5-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-2-(4-propylcyclohexyl)tetrahydropyran (13) (0.8 g) in 36% yield.

Workup

  1. customprepared in the tenth step
  2. customto give two layers
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (silica gel: 200 g, eluent: heptane/ethyl acetate=80/20 by volume)
  7. customby recrystallization (heptane/ethyl acetate=90/10 by volume)

Sources & evidence

ORD record
ord-4e55451ca81348b89f47abdd944d3a5b
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08389073B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes