Iodine → 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl phenyl ketone

HRID 1614890Notes

Reaction equation

[C:1]1(Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].C1C=CC=CC=1.[Mg].II.[CH3:18][C:19]1([CH3:35])[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[C:25]2[CH:24]=[C:23](C[N-]OC)[CH:22]=[CH:21][C:20]1=2.[Cl-].[NH4+].[CH2:38]([O:40]CC)C>O1CCCC1>[C:1]1([C:38]([C:23]2[CH:22]=[CH:21][C:20]3[C:19]([CH3:18])([CH3:35])[CH2:28][CH2:27][C:26]([CH3:29])([CH3:30])[C:25]=3[CH:24]=2)=[O:40])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The synthesis process is as set forth in the chemical reaction formula below. The PhBr in the reaction path stands for benzene bromide. To benzene bromide (1.17 g, 7.50 mmol) were added anhydrous tetrahydrofuran (10 mL), magnesium (911 mg, 37.5 mol) and iodine, followed by stirring at 80° C. After cooling down to room temperature, the mixture was added to 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl-N-methoxy-N-methylamide (J) (55.0 mg, 0.200 mmol) dissolved in anhydrous diethyl ether (2 mL), which was then stirred at room temperature for 22 hours. The reaction solution was poured into a saturated ammonium chloride aq. solution and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (2/1) as an elution solvent. The yield was 14.9 mg (25%).

Workup

temperatureAfter cooling down to room temperature
stirringwhich was then stirred at room temperature for 22 hours
extractionextracted by ethyl acetate
washThe organic layer was washed by water
dry with materiala saturated sodium hydrogen carbonate aq. solution and a saturated saline solution, dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-f4c34d7238b8448babdf4662d95d0502
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765719B2

Reaction notes

Loading…