Pyrrolidine → Chroman-2-ol

HRID 1030824

Reaktionsgleichung

Reaktionsgleichung von HRID 1030824
CC([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9]C=2)[C:5]=1[OH:14])=O.C12C(=[O:24])C(CCC1)CCC2.N1CCCC1>C1(C)C=CC=CC=1>[O:14]1[C:5]2[C:6](=[CH:11][CH:12]=[CH:13][CH:4]=2)[CH2:7][CH2:8][CH:9]1[OH:24]

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 697331'-Hydroxy-2'-acetonaphthoneHCID 86638Bicyclo(3.3.1)nonan-9-one

Produkt 1

HCID 11171070Chroman-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 8.29 g (0.06 mole) of bicyclo[3,3,1]nonan-9-one and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene, and the solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of this chromanol compound was heated at 150° C. to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes, and the obtained brown viscous liquid was purified by the chromatography on silica gel to obtain 6.9 g of a chromene compound represented by the following formula: ##STR161##

Aufarbeitung

  1. customA solution was prepared
  2. customwater was separated
  3. customAfter termination of the reaction, toluene
  4. customwas removed under reduced pressure
  5. customthe remaining chromanone compound was crystallized with acetone
  6. dissolutionThen, the chromanone compound was dissolved in 200 cc of methanol
  7. additionsodium boron hydride was gradually added to the solution

Quellen und Nachweise

ORD-Eintrag
ord-7b11dd9daecf49d79df7032be971b2de
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106998

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