Methyl Acrylate → Methyl indolizine-1-carboxylate

HRID 2272862Notes

Reaction equation

HRID 2272862 reaction equation
[Br-].[C:2]([CH2:5][NH+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH2:7]1)(O)=O.[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=C.C(N(CC)CC)C>C1(C)C=CC=CC=1.O=[Mn]=O>[C:13]1([C:12]([O:16][CH3:17])=[O:15])[CH:2]=[CH:5][N:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 117831258HCID 117831258, compound

Product 1

HCID 15474741Methyl indolizine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 6.55 g of the pyridinium salt obtained in Step A (30 mmol) in 240 mL of toluene there are added in succession 16.7 mL of methyl acrylate (150 mmol), 4.2 mL of triethylamine (30 mmol) and then, in portions, 20.9 g of MnO2 (240 mmol). The whole is subsequently heated at 90° C. for 3 hours. After cooling, the reaction mixture is filtered over a Celite cake and concentrated to dryness. The title product is then isolated by purification on silica gel (heptane/AcOEt gradient: 0-10%) in the form of an oil, which crystallises when cold.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered over a Celite cake
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d63bb35fbc5c4f129479c8dd0f3bec2c
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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