Acetonitrile → HCID 14652549, compound

HRID 2072700Notes

Reaction equation

HRID 2072700 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=[CH:6][CH:5]=1.[C:25](#[N:27])[CH3:26].[H-].[Na+]>CN(C)C=O.O1CCCC1>[O:2]=[C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=[CH:6][CH:5]=1)[CH2:26][C:25]#[N:27]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 10404365HCID 10404365, compound

Product 1

HCID 14652549HCID 14652549, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 10 g (30 mmol) of methyl-4-[2-(3,4,5-trimethoxyphenyl)ethyl]benzoate and 1.74 ml (33 mmol) of acetonitrile in a mixture of 30 ml of dry N,N-dimethylformamide and 20 ml of dry tetrahydrofuran was added, portionwise under a nitrogen atmosphere at 0° C., 3 g (76 mmol) of a 60% suspension of sodium hydride in mineral oil. The resulting suspension was heated under a flow of nitrogen to 65° C. and maintained at this temperature for 2 hours. After cooling to 25° C., the resultant mixture was quenched with 3 ml of methanol and the solvent was removed in vacuo. The resultant residue was dissolved in 60 ml of water, acidified with 2N hydrochloric acid to a pH between 4 and 5 and then extracted with ethyl acetate. The combined organic phase was then washed successively with water and saturated sodium chloride solution and dried over magnesium sulfate, after which time the solvent was removed under reduced pressure. The crude product was then purified on silica gel employing a mixture of ethyl acetate and hexane in a 1:1 ratio as the eluent to yield a white crystalline solid.

Workup

  1. additionwas added, portionwise under a nitrogen atmosphere at 0° C.
  2. temperaturemaintained at this temperature for 2 hours
  3. temperatureAfter cooling to 25° C.
  4. customthe resultant mixture was quenched with 3 ml of methanol
  5. customthe solvent was removed in vacuo
  6. dissolutionThe resultant residue was dissolved in 60 ml of water
  7. extractionextracted with ethyl acetate
  8. washThe combined organic phase was then washed successively with water and saturated sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. customafter which time the solvent was removed under reduced pressure
  11. customThe crude product was then purified on silica gel employing
  12. additiona mixture of ethyl acetate and hexane in a 1:1 ratio as the eluent
  13. customto yield a white crystalline solid

Sources & evidence

ORD record
ord-e8f8d541aaba403985b313e28f0e3985
Source dataset
uspto-grants-1990_04
Patent number
US04914096

Reaction notes

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