Water → HCID 86712403, compound

HRID 2174198Notes

Reaction equation

HRID 2174198 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][C:13]1[C:14]([C:19]([CH3:23])([CH3:22])[CH:20]=[O:21])=[N:15][CH:16]=[CH:17][CH:18]=1)=[CH:7]2.[CH3:24][Mg]Cl.O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][C:13]1[C:14]([C:19]([CH3:23])([CH3:22])[CH:20]([OH:21])[CH3:24])=[N:15][CH:16]=[CH:17][CH:18]=1)=[CH:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 86712402HCID 86712402, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 86712403HCID 86712403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

0.10 g of 2-[3-(8-fluoro-quinolin-3-yloxy)-pyridin-2-yl]-2-methyl-propioaldehyde were dissolved in 3 ml of tetrahydrofuran. 0.2 ml of a 3.0 M tetrahydrofuran solution of methylmagnesium chloride were added thereto followed by stirring for 30 minutes at 0° C. Subsequently, water was added thereto to stop the reaction. The resultant was then extracted with ethyl acetate followed by distilling off the solvent of the organic layer and purifying by silica gel column chromatography to obtain 0.07 g of 3-[3-(8-fluoro-quinolin-3-yloxy)-pyridin-2-yl]-3-methyl-butan-2-ol.

Workup

  1. customthe reaction
  2. extractionThe resultant was then extracted with ethyl acetate
  3. distillationby distilling off the solvent of the organic layer
  4. custompurifying by silica gel column chromatography

Sources & evidence

ORD record
ord-5b243470cf02412a861997cd0c809bb6
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

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