7'-Cyano-2'-methoxy-1'-acetonaphthone → 2-Cyano-8-isopropenyl-7-methoxynaphthalene

HRID 278042Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[I-].C[PH+](C)C.[C:12]([C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([O:27][CH3:28])=[C:21]2[C:24](=O)[CH3:25])=[CH:16][CH:15]=1)#[N:13]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:12]([C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[C:21]([C:24]([CH3:1])=[CH2:25])[C:20]([O:27][CH3:28])=[CH:19][CH:18]=2)[CH:23]=1)#[N:13]

Participants

Conditions

Temperature: 100 °C

Procedure

Under nitrogen atmosphere, 0.62 g of potassium t-butoxide was suspended in 10 ml of toluene, and 2.26 g of trimethylphosphonium iodide was added to the resulting suspension at room temperature. The resulting mixture was stirred under heating at 100° C. for one hour to give a yellow suspension. Then, 0.84 g of 7′-cyano-2′-methoxy-1′-acetonaphthone was added to the yellow suspension, and the resulting mixture was further stirred at 10° C. for 30 minutes, cooled to room temperature by allowing to stand, diluted with ethyl acetate, and filtered through Celite. The filtrate was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the resulting crude product was purified by silica gel column chromatography to give 0.78 g of the title compound as an oil.

Workup

customto give a yellow suspension
stirringthe resulting mixture was further stirred at 10° C. for 30 minutes
temperaturecooled to room temperature
filtrationfiltered through Celite
washThe filtrate was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated
customthe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-340908af97354c61a5bfe4f97ea3c171
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358995B1

Reaction notes

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