Water → [3-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]-2-methoxy-5,5-dimethyl-2-cyclohexenylidene]acetonitrile

HRID 85298Notes

Reaction equation

[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([N:18]([CH2:40][CH2:41][CH2:42][CH3:43])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27]2[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29](=O)[C:28]=2[O:36][CH3:37])=[C:21]([O:38][CH3:39])[CH:20]=1)[CH2:15][CH2:16][CH3:17].O>O1CCCC1.C(OCC)(=O)C>[CH2:14]([N:18]([CH2:40][CH2:41][CH2:42][CH3:43])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27]2[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29](=[CH:5][C:3]#[N:4])[C:28]=2[O:36][CH3:37])=[C:21]([O:38][CH3:39])[CH:20]=1)[CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To 0.18 g (7.5 mmol) of sodium hydride, 12 ml of tetrahydrofuran was added. To this mixture, 0.98 g (5.5 mmol) of diethyl cyanomethylphosphonate was added dropwise under ice cooling. To the mixture, 0.915 g (2.2 mmol) of 3-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]-2-methoxy-5,5-dimethyl-2-cyclohexenone in tetrahydrofuran was added dropwise. After the mixture was stirred at 60° C. for 24 hours, water was added to the mixture and extraction with ethyl acetate was performed. The extract was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 0.51 g of an orange oily matter (yield: 52.9%).

Workup

washThe extract was washed with a saturated saline solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography
customto give 0.51 g of an orange oily matter (yield: 52.9%)

Sources & evidence

ORD record: ord-ae009c67fda64de8a8808cb458df8387
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Reaction notes

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