Hydrochloric Acid → HCID 178447714, compound

HRID 439629Notes

Reaction equation

HRID 439629 reaction equation
[CH2:1]([Si:6]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:10][CH:9]([C:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:25]([C@H:28]1[CH2:33][CH2:32][C@H:31]([Mg]C2C=CC=CC=2)[CH2:30][CH2:29]1)[CH2:26][CH3:27].[Cl-].Cl>O1CCCC1>[CH2:1]([Si:6]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:10][CH:9]([C:12]2([C:17]3[CH2:16][CH2:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[CH:16][C:15]([C@H:31]3[CH2:30][CH2:29][C@H:28]([CH2:25][CH2:26][CH3:27])[CH2:33][CH2:32]3)=[CH:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22412509HCID 22412509, compoundHCID 178448104HCID 178448104, compound

Product 1

HCID 178447714HCID 178447714, compoundYield 139.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

34.1 g of 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)-3-cyclohexenone was dropped in 250 ml of a tetrahydrofuran solution of 0.5 moles of trans-(4-n-propylcyclohexyl)phenylmagnesium chloride, followed by agitation at room temperature for 5 hours. The resultant mixture was charged into diluted hydrochloric acid and extracted with ether. The resultant ether solution was washed with brine, dried and concentrated, followed by addition, to the resultant residue, of 300 ml of benzene and 800 mg of p-toluenesulfonic acid monohydrate and removal of generated water under reflux. When the generation of water stopped, the benzene solution was washed with brine, dried and concentrated, followed by purification through column chromatography to obtain 36.8 g of 1-(4-n-pentyl-4-phenyl-4-silacylohexyl)-4-(trans-4-n-propylcyclohexyl)phenyl-1,3-cyclohexadiene at a yield of 70%. The results of 1H-NMR analysis of the compound are shown below. 1H-NMR (CDCl3) δ:0.50-2.75(41H, m), 5.62-5.90(1H, m), 6.18-6.36(1H, m), 7.05-7.70(9H, m) ppm

Workup

  1. extractionextracted with ether
  2. washThe resultant ether solution was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. additionfollowed by addition, to the resultant residue, of 300 ml of benzene and 800 mg of p-toluenesulfonic acid monohydrate and removal of generated water
  6. temperatureunder reflux
  7. washthe benzene solution was washed with brine
  8. customdried
  9. concentrationconcentrated
  10. customfollowed by purification through column chromatography

Sources & evidence

ORD record
ord-52e32ee8542644e2acffdc41e6909fc7
Source dataset
uspto-grants-1996_05
Patent number
US05514824

Reaction notes

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