Dichloromethane → HCID 58535649, compound

HRID 1941730Notes

Reaction equation

HRID 1941730 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][CH2:34][CH2:35][CH3:36])[O:28][CH2:27]4)=[C:22]([F:37])[C:21]=3[F:38])=[C:16]([F:39])[C:15]=2[F:40])[CH2:9][CH2:8]1)[CH2:5][CH3:6]>O>[CH2:32]([CH:29]1[CH2:30][CH2:31][CH:26]([C:23]2[CH:24]=[CH:25][C:20]([C:17]3[CH:18]=[CH:19][C:14]([CH:10]4[CH2:9][CH2:8][CH:7]([CH2:4][CH2:5][CH3:6])[O:12][CH2:11]4)=[C:15]([F:40])[C:16]=3[F:39])=[C:21]([F:38])[C:22]=2[F:37])[CH2:27][O:28]1)[CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 58535762HCID 58535762, compound

Product 1

HCID 58535649HCID 58535649, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dichloromethane (10 ml) was added to 6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(6-pentyltetrahydro-2H-pyran-3-yl)biphenyl-4-yl)tetrahydro-2H-pyran-2-ol (21) (1.2 g) prepared in the second step. Tiethylsilane (0.27 g) and a boron trifluoride-diethyl ether complex (0.49 g) were added dropwise to the solution at −30° C. After 3 hours of stirring, water (10 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: 20 g, eluent: heptane/ethyl acetate=50/50 by volume), and then by recrystallization (heptane/ethyl acetate=90/10 by volume) to give 2-pentyl-5-(2,2′,3,3′-tetrafluoro-4′-(6-propyltetrahydro-2H-pyran-3-yl)biphenyl-4-yl)tetrahydro-2H-pyran (22) (0.3 g) in 25.8% yield.

Workup

  1. customprepared in the second step
  2. additionTiethylsilane (0.27 g) and a boron trifluoride-diethyl ether complex (0.49 g) were added dropwise to the solution at −30° C
  3. customto give two layers
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (silica gel: 20 g, eluent: heptane/ethyl acetate=50/50 by volume)
  8. customby recrystallization (heptane/ethyl acetate=90/10 by volume)

Sources & evidence

ORD record
ord-4839e8798e554f63acb80b997d0357e4
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

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