Acrylonitrile → HCID 67358715, compound

HRID 1667142Notes

Reaction equation

HRID 1667142 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]CC.[Na+].[C:23](#[N:26])[CH:24]=[CH2:25]>O1CCOCC1>[C:23]([CH2:24][CH2:25][C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:26]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 226748Ethyl diphenylacetateHCID 2723922Sodium ethoxide

Product 1

HCID 67358715HCID 67358715, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

The product of Example 68A (5.58 g) was dissolved in anhydrous dioxane (15 mL). Sodium ethoxide (1.58 g) was added and the mixture was heated to 40-50° C. for 30 minutes. Acrylonitrile (1.44 mL) was added dropwise with stirring. The mixture was heated at 60-70° C. for one hour. The dioxane was removed in vacuo, and the residue was taken up in diethyl ether, washed with water and brine, dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel chromatography (3-10% ethyl acetate/hexane) to obtain the title compound. MS (DCI+) m/z 311 (M+NH4)+.

Workup

  1. temperatureThe mixture was heated at 60-70° C. for one hour
  2. customThe dioxane was removed in vacuo
  3. washwashed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography (3-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0750a6269058423385fff15e797184dd
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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