Propan-2-one--water (1/1) → HCID 86732293, compound

HRID 930490Notes

Reaction equation

HRID 930490 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH3:14])[C:9]([CH:12]=C)=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4].CC(C)=[O:17].O>O=[Os](=O)(=O)=O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH3:14])[C:9]([CH:12]=[O:17])=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 18366337Propan-2-one--water (1/1)HCID 86732291HCID 86732291, compound

Product 1

HCID 86732293HCID 86732293, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

OsO4 (2.5 wt. % sol. in tert-Butanol) (0.86 mL, 0.0027 mol) was added to a stirred solution of 5-(but-2-yn-1-yloxy)-3-methyl-2-vinylpyridine (5.1 g, 0.027 mol) in acetone/water (100:100 mL) at 0° C. The reaction mixture was allowed to stir for 30 min at ambient temperature. Then NaIO4 (23.2 g, 0.108 mol) was added and the reaction mixture was allowed to stir for additional 4 h at ambient temperature. The reaction mixture was diluted with ice cold water (200 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel, eluting with 5-10% EtOAc in petroleum ether to give 5-(but-2-yn-1-yloxy)-3-methylpicolinaldehyde as an off white solid (3.6 g, 69.9%). MS m/z=189.9 [M+H]+.

Workup

  1. stirringto stir for additional 4 h at ambient temperature
  2. extractionextracted with EtOAc (3×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash column chromatography on silica gel
  7. washeluting with 5-10% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-0945d1eacb7c4e30bf8412423a229439
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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