Water → 6,7-Dimethyl-4-oxo-1,2,3,4-tetrahydrophenanthrene

HRID 375012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375012
CC([O-])(C)C.[K+].[CH3:7][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][C:21]=1[CH3:22])[CH:18]=[CH:17][C:16]1[CH2:15][CH2:14][CH2:13][C:12](=[O:23])[C:11]2=1.[CH2:24](I)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=[CH2:34].O>C1C=CC=CC=1>[CH3:7][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][C:21]=1[CH3:22])[CH:18]=[CH:17][C:16]1[CH2:15][CH2:14][CH:13]([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=[CH2:24])[C:12](=[O:23])[C:11]2=1.[CH3:7][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][C:21]=1[CH3:22])[CH:18]=[CH:17][C:16]1[CH2:15][CH2:14][CH2:13][C:12](=[O:23])[C:11]2=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 1111946211-Iodoundec-1-eneHCID 229045956,7-Dimethyl-4-oxo-1,2,3,4-tetrahydrophenanthreneHCID 23665647Potassium tert-butoxide

Produkt 2

HCID 229045886,7-Dimethyl-4-oxo-3-(10-undecenyl)-1,2,3,4-tetrahydrophenanthreneAusbeute 39 %HCID 229045956,7-Dimethyl-4-oxo-1,2,3,4-tetrahydrophenanthreneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

t-BuOK (3.6 g, 0.032 mole) was dissolved in 250 ml of dry benzene at 40°-50° C. To the stirred solution was added 6,7-Dimethyl-4-oxo-1,2,3,4-tetrahydrophenanthrene (3.6 g, 0.016 mole) in 50 ml of dry benzene and then, 10-undecenyl iodide (4.58 g, 0.016 mole) at 30° C. under N2. The mixture was heated to 60° C. for 2.5 hr under N2. After cooling the reaction mixture to room temperature, water was added. The whole mixture was extracted twice with diethylether. The combined diethylether solution was dried over anhydrous MgSO4 and then concentrated. Flash column chromatography of the residue on silica gel afforded 6,7-Dimethyl-4-oxo-3-(10-undecenyl)-1,2,3,4-tetrahydrophenanthrene as a sticky brown solid (2.36 g, 0.0063 mole, 39% yield) as a desired product, and unreacted 6,7-Dimethyl-4-oxo-1,2,3,4-tetrahydrophenanthrene (1.70 g, 47% recovered). 1H NMR (CDCl3)δ 1.29-1.62 (m,14H), 1.86-2.08 (m,4H), 2.21-2.35 (m,2H), 2.40 (s,3H), 2.46 (s,3H), 2.52-2.63 (m,1H), 3.07-3.13 (m,2H), 4.90-5.04 (m,2H), 5.75-5.89 (m,1H), 7.17 (d, J=8.2 Hz,1H), 7.53 (s,1H), 7.77 (d, J=8.2 Hz,1H), 9.10 (s,1H), IR (KBr) cm-1 2920, 2850, 1669, 1600, exact (EI) mass. calcd. for C27H36O: 376.2766, Found: 376.2766.

Aufarbeitung

  1. customat 30° C.
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. extractionThe whole mixture was extracted twice with diethylether
  4. dry with materialThe combined diethylether solution was dried over anhydrous MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a0db89e094b44644acf1d5e3c1adcb53
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484530

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