Ethyl Acetate → HCID 21074638, compound

HRID 1374441Notes

Reaction equation

HRID 1374441 reaction equation
C([N:8]1[CH:13]([CH3:14])[CH2:12][CH:11]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)C1C=CC=CC=1.Cl[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21].C(=O)([O-])O.[Na+].C(OCC)(=O)C>C1COCC1>[CH3:14][CH:13]1[N:8]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH2:9][C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH2:12]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 18052Allyl chloroformateHCID 516892Sodium BicarbonateHCID 17857898HCID 17857898, compound

Product 1

HCID 21074638HCID 21074638, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-benzyl-6-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate (2.05 g, 8.36 mmol) in THF (15 ml) were added at 0–5° C. allyl chloroformate (1.1 ml, 10.4 mmol). The mixture was immediately raised to room temperature and stirred for 18 hours. After cooled to 0–5° C. a saturated aqueous sodium hydrogen carbonate and ethy acetate were added thereto and the mixture was separated with a separating funnel. The aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent was removed in vacuo. The residue was purified with silica gel (55 g) chromatography (hexane/ethyl acetate=6/1→4/1) to give 1-allyl 3-methyl 6-methyl-5,6-dihydro-1,3(2 H)-pyridinedicarboxylate (1.42 g, 71%).

Workup

  1. additionwere added
  2. customthe mixture was separated with a separating funnel
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified with silica gel (55 g) chromatography (hexane/ethyl acetate=6/1→4/1)

Sources & evidence

ORD record
ord-2122ccc06c33489d98a790eb01df5d41
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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