3,4-dihydro-2H-pyran → HCID 178418655, Verbindung

HRID 5303

Reaktionsgleichung

Reaktionsgleichung von HRID 5303
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.S(O[Si](C)(C)C)(O[Si](C)(C)C)(=O)=O>ClCCl>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 87573Silanol, trimethyl-, 1,1'-sulfateHCID 178418615HCID 178418615, Verbindung

Produkt 1

HCID 178418655HCID 178418655, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3.0 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol, 1.1 ml of 3,4-dihydro-2H-pyran in 30 ml of dichloromethane was treated at 0° C. with a solution of 0.007 g of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at 0° C. for a further 30 minutes and then washed once with sodium carbonate solution and twice with water and subsequently dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1). Recrystallization from ethyl acetate at -20° C. gave 1.75 g of pure trans-4-(4'-cyano-4-biphenylyl)cyclohexyl tetrahydropyranyl ether.

Aufarbeitung

  1. washwashed once with sodium carbonate solution and twice with water
  2. dry with materialsubsequently dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9:1)
  6. customRecrystallization from ethyl acetate at -20° C.

Quellen und Nachweise

ORD-Eintrag
ord-5e5c25f893b444bd9bf8ae43f97a4d3f
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244597

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