Sodium benzenethiolate → 1-Phenylmercapto-2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene

HRID 3898

Reaktionsgleichung

Reaktionsgleichung von HRID 3898
C(O[CH2:5][C:6]([CH3:27])=[CH:7][CH:8]=[C:9]([CH3:26])[CH:10]=[CH:11][CH:12]=[C:13]([CH3:25])[CH:14]=[CH:15][C:16]1[C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:17]=1[CH3:24])(=O)C.[S-:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Na+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.C(OCC)C>[C:29]1([S:28][CH2:5][C:6]([CH3:27])=[CH:7][CH:8]=[C:9]([CH3:26])[CH:10]=[CH:11][CH:12]=[C:13]([CH3:25])[CH:14]=[CH:15][C:16]2[C:21]([CH3:22])([CH3:23])[CH2:20][CH2:19][CH2:18][C:17]=2[CH3:24])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

6

Edukt 2

HCID 4110039Sodium benzenethiolateHCID 544237292,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl acetate

Produkt 1

HCID 536691651-Phenylmercapto-2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

To a solution of 1.85 g (5 mmol) of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl acetate in 25 ml of anhydrous THF and 8 ml of HMPA is added in portions 0.68 g (5.2 mmol) of sodium thiophenoxide. The resulting mixture is stirred at room temperature for 18 hours and then taken up in 250 ml of diethyl ether. The solution is washed with saturated aqueous NH4Cl and water, dried annd evaporated in vacuo to give an oil. Purification on a silica gel dry column gives the desired product.

Aufarbeitung

  1. washThe solution is washed with saturated aqueous NH4Cl and water
  2. customdried
  3. customannd evaporated in vacuo
  4. customto give an oil
  5. customPurification on a silica gel
  6. customdry column

Quellen und Nachweise

ORD-Eintrag
ord-32560364bc2c4583929e9619527c24ce
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04722939

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