Dichloromethane → HCID 58535319, compound

HRID 1941728Notes

Reaction equation

HRID 1941728 reaction equation
ClCCl.[CH2:4]([CH:7]1[O:12][CH:11](O)[CH:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]4[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][CH3:34])[CH2:28][CH2:27]4)=[C:22]([F:35])[C:21]=3[F:36])=[C:16]([F:37])[C:15]=2[F:38])[CH2:9][CH2:8]1)[CH2:5][CH3:6].C([SiH](CC)CC)C>O>[CH2:4]([CH:7]1[CH2:8][CH2:9][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]4[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][CH3:34])[CH2:28][CH2:27]4)=[C:22]([F:35])[C:21]=3[F:36])=[C:16]([F:37])[C:15]=2[F:38])[CH2:11][O:12]1)[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12052TriethylsilaneHCID 58535291HCID 58535291, compound

Product 1

HCID 58535319HCID 58535319, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dichloromethane (40 ml) was added to 6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(4-propylcyclohexyl)biphenyl-4-yl)tetrahydro-2H-pyran-2-ol (17) (4.2 g) prepared in the second step. Triethylsilane (1.01 g) and a boron trifluoride-diethyl ether complex (1.82 g) were added dropwise to the solution at −30° C. After 3 hours of stirring, water (40 ml) was added to give two layers. The organic layer was washed with water and 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 2-propyl-5-(2,2′,3,3′-tetrafluoro-4′-(4-propylcyclohexyl)biphenyl-4-yl)tetrahydro-2H-pyran (18) (1.8 g) in 44.3% yield.

Workup

  1. customprepared in the second 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-494ee086fa9f428dbf6f95c04842b6b8
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

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