Hexane → HCID 20309506, compound

HRID 1763312Notes

Reaction equation

HRID 1763312 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.C([Li])CCC.CCCCCC.[CH3:22][N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29]>O1CCCC1>[CH3:22][NH:23][C:24](=[O:29])[CH2:25][CH2:26][C:27](=[O:28])[C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 8058HexaneHCID 90251,3-DimethoxybenzeneHCID 707172,5-Pyrrolidinedione, 1-methyl-HCID 178418339Butyllithium

Product 1

HCID 20309506HCID 20309506, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,3-dimethoxybenzene (89 ml, 0.064 mole) in dry tetrahydrofuran (480 ml) was added during 10 minutes to a stirred solution of n-butyl lithium in hexane (350 ml, 0.6 mole) under an atmosphere of nitrogen. The stirred mixture was heated under reflux for 90 minutes, then a solution of N-methyl succinimide (77 g, 0.68 mole) in dry tetrahydrofuran was added dropwise. The mixture was heated under reflux for an additional hour and then allowed to stand overnight. The supernatant was decanted and the residue was hydrolysed with 20% aqueous ammonium chloride solution (280 ml) and extracted with chloroform. The washed and dried extract was evaporated and the residue recrystallised from ethyl acetate to give N-methyl 3-(2,6-dimethoxybenzoyl)-propionamide (15 g, 10%, m.p. 134° ). (Found: C, 62.18; H, 6.73; N, 5.54; C13H17NO4 requires C, 62.14; H, 6.82; N, 5.57%).

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 90 minutes
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for an additional hour
  5. customThe supernatant was decanted
  6. extractionextracted with chloroform
  7. washThe washed
  8. customdried
  9. extractionextract
  10. customwas evaporated
  11. customthe residue recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-af8e3b06dd6842f0890bf31535f8b072
Source dataset
uspto-grants-1978_09
Patent number
US04111936

Reaction notes

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