Sodium Methoxide → HCID 11658792, compound

HRID 424976Notes

Reaction equation

HRID 424976 reaction equation
C(OC([N:8]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]1[CH2:22][CH2:23][CH2:24][OH:25])=O)(C)(C)C.C[O-].[Na+]>CO>[CH:13]([C:12]1[NH:8][C:9]([CH2:22][CH2:23][CH2:24][OH:25])=[C:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11595361HCID 11595361, compound

Product 1

HCID 11658792HCID 11658792, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml flask containing compound 15 (0.197 g, 0.57 mmol), 3.7 ml (8.7 mmol) of a 2.33 M solution of anhydrous sodium methanolate in methanol are added. The solution is left stirring at ambient temperature for 72 h. The solvent is then evaporated with a rotary evaporator. 5 ml of an aqueous solution saturated with ammonium chloride are added to the residue obtained. The solution thus obtained is extracted with ether. After separation of the phases, the organic phase is washed with brine then dried on MgSO4. After separation of the magnesium salts by filtration, the ether is evaporated. The residue obtained is purified by chromatography on a silica gel column (AcOEt/heptane 1/2 in volume, Rf 0.1). Compound 18 is isolated with a yield of 86.4% (0.121 g) in the form of a brown oil.

Workup

  1. additionare added
  2. waitThe solution is left
  3. customThe solvent is then evaporated with a rotary evaporator
  4. addition5 ml of an aqueous solution saturated with ammonium chloride are added to the residue
  5. customobtained
  6. customThe solution thus obtained
  7. extractionis extracted with ether
  8. customAfter separation of the phases
  9. washthe organic phase is washed with brine
  10. customthen dried on MgSO4
  11. customAfter separation of the magnesium salts
  12. filtrationby filtration
  13. customthe ether is evaporated
  14. customThe residue obtained
  15. customis purified by chromatography on a silica gel column (AcOEt/heptane 1/2 in volume, Rf 0.1)

Sources & evidence

ORD record
ord-c6265f5f73d64de7b5b6c0a8e0a25b34
Source dataset
uspto-grants-2012_01
Patent number
US08106089B2

Reaction notes

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