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

HRID 85293Notes

Reaction equation

[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([N:18]([CH2:38][CH2:39][CH2:40][CH3:41])[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)[CH:28]=2)=[C:21]([O:36][CH3:37])[CH:20]=1)[CH2:15][CH2:16][CH3:17].O>O1CCCC1>[CH2:38]([N:18]([CH2:14][CH2:15][CH2:16][CH3:17])[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])[CH:28]=2)=[C:21]([O:36][CH3:37])[CH:20]=1)[CH2:39][CH2:40][CH3:41]

Participants

Conditions

Temperature: 50 °C

Procedure

To 0.23 g (9.6 mmol) of sodium hydride, 20 ml of tetrahydrofuran was added. To this mixture, 1.39 g (7.85 mmol) of diethyl cyanomethylphosphonate was added dropwise under ice cooling. To the mixture, 1.21 g (3.15 mmol) of 3-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]-5,5-dimethyl-2-cyclohexenone in tetrahydrofuran was added dropwise. After the reaction mixture was stirred at 50° C. overnight, water was added thereto 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 1.05 g of an orange oily matter (yield: 82.0%).

Workup

extractionextraction with ethyl acetate
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 1.05 g of an orange oily matter (yield: 82.0%)

Sources & evidence

ORD record: ord-b07ec92e91f548d79f8a5de7628d114c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Reaction notes

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