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

HRID 1488329Notes

Reaction equation

HRID 1488329 reaction equation
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

Participants

7

Reactant 4

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-961409ea418b45199d6f0a2d80afad19
Source dataset
uspto-grants-1997_10
Patent number
US05674387

Reaction notes

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