Ammonium Chloride → 4-(4-Chlorophenyl)-1-phenyl-1-n-propyl-1-silacyclohex-3-ene

HRID 1684445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684445
[CH2:1]([Si:4]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Cl)=[CH:20][CH:19]=1.[Cl-].[NH4+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1C=CC=CC=1.O1CCCC1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:7]2[CH2:8][CH2:9][Si:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)([CH2:1][CH2:2][CH3:3])[CH2:5][CH:6]=2)=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 118313174-Propyl-4-phenyl-4-silacyclohexanoneHCID 178478983HCID 178478983, Verbindung

Produkt 1

HCID 190391334-(4-Chlorophenyl)-1-phenyl-1-n-propyl-1-silacyclohex-3-ene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

10.0 g of 4-n-propyl-4-phenyl-4-silacyclohexanone was dripped into a 50 ml tetrahydrofuran solution of 1.0M p-chlorophenyl magnesium chloride at 40°-50° C. After stirring for 2 hours at 50° C., the mixture was poured into a saturated aqueous solution of ammonium chloride and extraction was conducted using benzene. 500 mg of p-toluenesulfonic acid monohydrate was then added to the benzene solution and refluxing was conducted while the water generated was distilled away. After the water stopped distilling away, the benzene layer was washed with an aqueous solution of sodium bicarbonate, dried and concentrated to obtain 4-(4-chlorophenyl)-1-phenyl-1-n-propyl-1-silacyclohex-3-ene. This was then dissolved in 50 ml of ethanol and hydrogenation was conducted using 1.0 g of palladium carbon as a catalyst. After the catalyst was filtered out, the product was concentrated to obtain 14.0 g of 4-(4-chlorophenyl)-1-phenyl-1-n-propyl-1-silacyclohexane.

Aufarbeitung

  1. temperaturerefluxing
  2. distillationgenerated was distilled away
  3. distillationAfter the water stopped distilling away
  4. washthe benzene layer was washed with an aqueous solution of sodium bicarbonate
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b8fa0081655b473a8960d4689d72c0b8
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05641431

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