Iodine → HCID 58535467, compound

HRID 1941731Notes

Reaction equation

HRID 1941731 reaction equation
[Mg].II.Br[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[C:15]([F:22])[C:14]=2[F:23])=[C:9]([F:24])[C:8]=1[F:25].C([CH:29]1[O:34][C:33](=O)[CH:32]([C:36]2[CH:41]=[CH:40][C:39]([C:42]3C=CC(C4CCC(CCCCC)OC4)=[C:44](F)[C:43]=3F)=[C:38](F)[C:37]=2F)[CH2:31][CH2:30]1)CC.C1C[O:66]CC1>>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:29]3([OH:66])[CH2:30][CH2:31][CH:32]([CH:36]4[CH2:41][CH2:40][CH:39]([CH2:42][CH2:43][CH3:44])[CH2:38][CH2:37]4)[CH2:33][O:34]3)=[C:8]([F:25])[C:9]=2[F:24])=[C:14]([F:23])[C:15]=1[F:22])[CH3:21]

Participants

6

Reactant 5

HCID 807IodineHCID 8028Tetrahydrofuran3×HCID 5462224MagnesiumHCID 58535544HCID 58535544, compoundHCID 58535698HCID 58535698, compound

Product 1

HCID 58535467HCID 58535467, compoundYield 47.1%

Conditions

Temperature
-30 °C

Procedure

THF (5 ml) was added to magnesium turnings (0.30 g) in a reaction vessel under an atmosphere of nitrogen, and a minute amount of iodine was added. 4-(2-Bromoethyl)-4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl (29) (4.60 g) in a THF (5 ml) solution was slowly added dropwise at a temperature 50° C. or lower. After the addition had been completed, the stirring was continued at room temperature for 30 minutes. The reaction mixture was then cooled to −30° C. or lower, and 5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-one (20) (2.46 g) in a THF (5 ml) solution was added dropwise. After the reaction mixture had been stirred at room temperature for 5 hours, it was quenched with a saturated aqueous solution of ammonium chloride, and water (20 ml) was added to give two layers. The water layer was extracted with toluene (10 ml) twice, and the combined organic layer was washed with water and then 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: toluene/ethyl acetate=70/30 by volume) to give 2-(2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)ethyl)-5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-ol (30) (2.7 g) in 47.1% yield.

Workup

  1. additionAfter the addition
  2. customit was quenched with a saturated aqueous solution of ammonium chloride, and water (20 ml)
  3. additionwas added
  4. customto give two layers
  5. extractionThe water layer was extracted with toluene (10 ml) twice
  6. washthe combined organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel chromatography (silica gel: 20 g, eluent: toluene/ethyl acetate=70/30 by volume)

Sources & evidence

ORD record
ord-53b9c08f8a8c4b7f8c4743c3b7fbb1b7
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

Loading…