Sodium hydride → HCID 178471921, compound

HRID 1382266Notes

Reaction equation

HRID 1382266 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH:19]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCCC1>[CH:19]1([C:25]([C:13](=[CH:12][NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH3:3])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75938Cyclohexanecarbonyl chlorideHCID 67899433Ethyl3-(2-methoxyphenylamino)acrylate

Product 1

HCID 178471921HCID 178471921, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

50% Sodium hydride (4.8 g, 0.1 mol) was washed with petroleum ether then stirred in dry tetrahydrofuran (50 ml) under nitrogen at -20° C. Ethyl 3-(2-methoxyphenylamino)acrylate (17.4 g, 0.1 mol) in dry tetrahydrofuran 100 ml) was added dropwise, keeping the temperature to -20° C. Cooling was removed and the mixture was stirred until a dark red colour was achieved. The mixture was recooled to -20° C. and cyclohexylcarbonyl chloride (14.0 ml, 0.1 mol) in dry tetrahydrofuran (50 ml) was added dropwise. The mixture was allowed to warm to room temperature and was stirred for a further 3 hours. The solvent was evaporated and the residue was partitioned between dichloromethane and 2M HCl. The organic layer was washed with water and brine, dried and evaporated to an oil which was chromatographed (silica gel, dichloromethane-hexane) to afford ethyl 2-cyclohexylcarbonyl-3-(2-methoxyphenylamino)acrylate as a yellow oil (23.3 g, 70%).

Workup

  1. customto -20° C
  2. temperatureCooling
  3. customwas removed
  4. customwas recooled to -20° C.
  5. stirringwas stirred for a further 3 hours
  6. customThe solvent was evaporated
  7. customthe residue was partitioned between dichloromethane and 2M HCl
  8. washThe organic layer was washed with water and brine
  9. customdried
  10. customevaporated to an oil which
  11. customwas chromatographed (silica gel, dichloromethane-hexane)

Sources & evidence

ORD record
ord-95007b5cc25643fa931a6f9e6579e80d
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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