Pyridine → HCID 178418683, Verbindung

HRID 5305

Reaktionsgleichung

Reaktionsgleichung von HRID 5305
O1CCCCC1[O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1.S(O[Si](C)(C)C)(O[Si](C)(C)C)(=O)=O.N1C=CC=CC=1>CO.C(OCC)C.ClCCl>[CH2:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[CH:16]=[CH:15][C:14]([C@H:11]3[CH2:12][CH2:13][C@H:8]([OH:7])[CH2:9][CH2:10]3)=[CH:19][CH:18]=2)=[CH:25][CH:24]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 87573Silanol, trimethyl-, 1,1'-sulfateHCID 178418673HCID 178418673, Verbindung

Produkt 1

HCID 178418683HCID 178418683, VerbindungAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.2 ml of pyridine. Subseguently, the reaction mixture was concentrated and the residue was then taken up in 50 ml of dichloromethane, washed twice with water, dried over magnesium sulfate, filtered and again concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from methanol gave 0.5 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexanol.

Aufarbeitung

  1. concentrationSubseguently, the reaction mixture was concentrated
  2. washwashed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationagain concentrated
  6. customThe residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
  7. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-5644e5fd1d534b5297d22337a4455595
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244597

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