Water → 5-(4-Dibutylamino-2-methoxyphenyl)-2,4-pentadienenitrile

HRID 85281Notes

Reaction equation

HRID 85281 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([N:18]([CH2:31][CH2:32][CH2:33][CH3:34])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][CH:27]=O)=[C:21]([O:29][CH3:30])[CH:20]=1)[CH2:15][CH2:16][CH3:17].O>O1CCCC1>[CH2:14]([N:18]([CH2:31][CH2:32][CH2:33][CH3:34])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][CH:27]=[CH:5][C:3]#[N:4])=[C:21]([O:29][CH3:30])[CH:20]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 866675703-(4-Dibutylamino-2-methoxyphenyl)propenal

Product 1

HCID 866675735-(4-Dibutylamino-2-methoxyphenyl)-2,4-pentadienenitrileYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 200 mg (8.3 mmol) of sodium hydride, 14 ml of tetrahydrofuran was added. To this mixture, 1.47 g (8.3 mmol) of diethyl cyanomethylphosphonate was added dropwise under ice cooling, and the mixture was stirred for 20 minutes. Next, 1.02 g (3.52 mmol) of 3-(4-dibutylamino-2-methoxyphenyl)propenal in tetrahydrofuran was added dropwise. After stirred for 30 minutes, the reaction mixture was poured into 100 ml of water and subjected to extraction with ethyl acetate. 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 1.0 g of an orange oily matter (yield: 91.2%).

Workup

  1. stirringAfter stirred for 30 minutes
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extract was washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. customto give 1.0 g of an orange oily matter (yield: 91.2%)

Sources & evidence

ORD record
ord-0532b1d1a0b946a991e148c549f7de82
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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