1,4-Dioxane → HCID 86707562, compound

HRID 339099Notes

Reaction equation

HRID 339099 reaction equation
[F:1][C:2]1[C:3]([CH3:18])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][C@H:14]([O:16][CH3:17])[CH3:15])[CH:6]=2.[O:19]1CCOCC1>O>[F:1][C:2]1[C:3]([CH:18]=[O:19])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][C@H:14]([O:16][CH3:17])[CH3:15])[CH:6]=2

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 70983644HCID 70983644, compound

Product 1

HCID 86707562HCID 86707562, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (R)-3-fluoro-7-(2-methoxypropoxy)-2-methylquinoline (0.030 g, 0.120 mmol) and SeO2 (0.0160 g, 0.144 mmol) in dioxane (10 mL) and water (0.1 mL) was stirred at 102° C. (bath) for 5 hours. The solid was removed by filtration. The mother liquor was concentrated under reduced pressure. The residue obtained was purified by flash chromatography 2.5:1 hexane/ethyl acetate to give (R)-3-fluoro-7-(2-methoxypropoxy)quinoline-2-carbaldehyde (0.024 g, 0.091 mmol, 76% yield) as a solid.

Workup

  1. customThe solid was removed by filtration
  2. concentrationThe mother liquor was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas purified by flash chromatography 2.5:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-283f7f66e0e84db48c0b30f54869ca4c
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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