HCID 59497296, compound → HCID 86645720, compound

HRID 1747444Notes

Reaction equation

HRID 1747444 reaction equation
[CH3:1][C:2]1[N:10]2[C:5]([C:6]([CH3:11])=[CH:7][CH:8]=[CH:9]2)=[C:4]([CH2:12][OH:13])[CH:3]=1>CC(C)=O.O=[Mn]=O>[CH3:1][C:2]1[N:10]2[C:5]([C:6]([CH3:11])=[CH:7][CH:8]=[CH:9]2)=[C:4]([CH:12]=[O:13])[CH:3]=1

Participants

4

Reactant 1

HCID 59497296HCID 59497296, compound

Product 1

HCID 86645720HCID 86645720, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent

Procedure

To a solution (3,8-Dimethyl-indolizin-1-yl)-methanol (600 mg, 3.4 mmol) in acetone (20 mL) was added MnO2 (595 mg, 6.8 mmol) at room temperature. The mixture was stirred at the same temperature for 3 hours. The solution was filtered and the filtrate was concentrated. The residue was purified by CombiFlash with 5% EtOAc in Hexane as the eluent to afford the desirable product 3,8-Dimethyl-indolizine-1-carbaldehyde (400 mg, 67%) as a grey solid.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by CombiFlash with 5% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-18a8d140cb3b4cf5860c9aee1568e783
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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