Sodium hydride → HCID 178471922, compound

HRID 1382279Notes

Reaction equation

HRID 1382279 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:18])[CH:7]=[CH:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])[CH3:4].[C:19](Cl)(=[O:23])[CH:20]([CH3:22])[CH3:21]>O1CCCC1>[C:19]([C:7](=[CH:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])[C:6]([O:5][CH2:3][CH3:4])=[O:18])(=[O:23])[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62325Isobutyryl chlorideHCID 67899433Ethyl3-(2-methoxyphenylamino)acrylate

Product 1

HCID 178471922HCID 178471922, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

50% Sodium hydride (4.8 g, 0.1 mol) was washed with petroleum ether and suspended in dry tetrahydrofuran (50 ml) under nitrogen at -10° C. Ethyl3-(2-methoxyphenylamino)acrylate (22.4 g. 0.1 mol) in dry tetrahydrofuran (70 ml) was added dropwise to the suspension keeping the temperature to below 0° C. Cooling was removed and the mixture was stirred at ambient temperature until a deep orange colour was obtained. The mixture was recooled to -20° C. and treated dropwise with a solution of isobutyryl chloride (11.0 ml, 0.11 mol) in dry tetrahydrofuran (30 ml). The cooling bath was again removed, and the mixture stirred overnight at room temperature. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with dilute hydrochloric acid and brine, dried, filtered and evaporated. The crude product was chromatographed (silica gel, petroleum ether/dichloromethane) to afford ethyl 2-isobutyryl-3-(2-methoxyphenylamino)acrylate as an oil (22.6 g, 77.5%).

Workup

  1. customto below 0° C
  2. temperatureCooling
  3. customwas removed
  4. customwas obtained
  5. customwas recooled to -20° C.
  6. customThe cooling bath was again removed
  7. stirringthe mixture stirred overnight at room temperature
  8. customThe solvent was evaporated
  9. dissolutionthe residue was dissolved in dichloromethane
  10. washwashed with dilute hydrochloric acid and brine
  11. customdried
  12. filtrationfiltered
  13. customevaporated
  14. customThe crude product was chromatographed (silica gel, petroleum ether/dichloromethane)

Sources & evidence

ORD record
ord-94643ded060443b7af290eba68adb975
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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