Water → 3-(1-Triphenylmethylimidazol-2-yl)-1-(tetrahydropyran-2-yloxy)propane

HRID 638324

Reaktionsgleichung

Reaktionsgleichung von HRID 638324
[C:1]1([C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.I[CH2:31][CH2:32][CH2:33][O:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][O:36]1.O>C1COCC1.CCCCCC>[C:19]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH2:31][CH2:32][CH2:33][O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 618231DechloroclotrimazoleHCID 110329072-(3-iodopropoxy)tetrahydro-2H-pyranHCID 178418339Butyllithium

Produkt 1

HCID 202534833-(1-Triphenylmethylimidazol-2-yl)-1-(tetrahydropyran-2-yloxy)propane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 310 mg (1 mmol) of 1-triphenylmethylimidazole (K H. Buchel et al.; Drugs Made in Germany, 1972, 15, 77) in 12 ml of dry THF is cooled to 0° under nitrogen and treated with 0.647 ml (1.1 mmol) of 1.7M solution of n-BuLi in hexane. The solution is stirred at room temperature for 1 hour, then recooled to 0° and treated with 405 mg (1.5 mmol) of 1-iodo-3-(tetrahydropyran-2-yloxy)propane dissolved in 2 ml of dry THF. The reaction mixture is allowed to warm to room temperature overnight, then poured into water and extracted with ethyl acetate. The organic extract is rinsed with brine and dried (MgSO4). Removal of solvents in vacuo affords the title A compound.

Aufarbeitung

  1. customrecooled to 0°
  2. temperatureto warm to room temperature overnight
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washis rinsed with brine
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvents in vacuo
  8. customaffords the title A compound

Quellen und Nachweise

ORD-Eintrag
ord-8c99b2965d3f401d90ccab40f4d33597
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560680

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