Sodium Chloride → HCID 178505689, Verbindung

HRID 1419656

Reaktionsgleichung

Reaktionsgleichung von HRID 1419656
[K].CCSC(N(CC(C)C)CC(C)C)=O.[O:16]1[C:20]2([CH2:25][CH2:24][CH:23]([CH:26]3[CH2:31][CH2:30][CH:29]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=4)[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1.[Cl-].[Na+]>CS(C)=O>[O:16]1[C:20]2([CH2:25][CH2:24][CH:23]([C@H:26]3[CH2:31][CH2:30][C@H:29]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=4)[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 16181ButylateHCID 5462222PotassiumHCID 213085884-(1,4-Dioxaspiro[4,5]dec-8-yl)-1-(3-fluorophenyl)-cyclohexane

Produkt 1

HCID 178505689HCID 178505689, VerbindungAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

23.7 g of potassium t.-butylate were added to a solution of 125.3 g of 4-(1,4-dioxaspiro[4,5]dec-8-yl)-1-(3-fluorophenyl)-cyclohexane (cis/trans 50/47) in 630 ml of dimethyl sulphoxide, the mixture was stirred at 100° C. for 2 hrs., cooled and poured into 2500 ml of 5 percent sodium chloride solution. The reaction mixture was extracted with methylene chloride, the organic phase was dried over sodium sulfate, filtered and the filtrate was evaporated. Crystallization of the residue from isopropanol gave 121.9 g of trans-4-(1,4-dioxaspiro[4,5]dec-8-yl)-1-(3-fluorophenyl)cyclohexane as colorless crystals (trans content 99.8%).

Aufarbeitung

  1. temperature, cooled
  2. extractionThe reaction mixture was extracted with methylene chloride
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate was evaporated
  6. customCrystallization of the residue from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-5ec8769642e9475c888caa24dee08499
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05888423

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