Dimethylformamide → HCID 19848548, compound

HRID 1608131Notes

Reaction equation

HRID 1608131 reaction equation
[C:1](CP(=O)(OCC)OCC)#[N:2].[H-].[Na+].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:27][CH2:28][C:29]#[CH:30])[C:22]=1[O:23][CH2:24][C:25]#[CH:26])[CH:18]=O.[CH3:31]N(C)C=O>>[Cl:14][C:15]1[CH:16]=[C:17]([C:18](=[CH2:31])[C:1]#[N:2])[CH:20]=[C:21]([O:27][CH2:28][C:29]#[CH:30])[C:22]=1[O:23][CH2:24][C:25]#[CH:26]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 141303053-Chloro-4,5-dipropargyloxybenzaldehyde

Product 1

HCID 19848548HCID 19848548, compound

Conditions

Temperature
0 °C

Procedure

Diethyl cyanomethylphosphonate (1.42 g) was dissolved in dimethylformamide (50 ml), and sodium hydride (0.32 g; 60% dispersion in mineral oil) was added thereto at 0° C. under cooling. After the foaming ceased, 3-chloro-4,5-dipropargyloxybenzaldehyde (2.00 g) was added to the reaction mixture, which was stirred at room temperature overnight, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 2-(3-chloro-4,5-dipropargyloxyphenyl)acrylonitrile (1.85 g). m.p., 110°-111° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a2e255e368204d96a0ec75e55841ce3d
Source dataset
uspto-grants-1989_09
Patent number
US04870064

Reaction notes

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