Water → HCID 12919964, compound

HRID 2379679Notes

Reaction equation

HRID 2379679 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]([CH3:23])[C:19](OC)=[O:20])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.OS(O)(=O)=O>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:23])[CH2:19][OH:20])=[CH:24][CH:25]=1)[CH:6]=[N:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 186933Methyl 2-{4-[(6-fluoroquinoxalin-2-yl)oxy]phenoxy}propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12919964HCID 12919964, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In 50 ml. anhydrous ethyl ether, 0.5 g. (1.5 m mol) of methyl 2-[4-(6-fluoro-2-quinoxalyloxy)phenoxy]propionate was dissolved and 10 ml. of a solution containing 0.11 g. (3.0 m mol) of LiAlH4 in anhydrous ethyl ether was added dropwise and the mixture was refluxed for 12 hours. After the reaction, 10 ml. of water and 7 ml. of 2N-H2SO4 were added to the reaction mixture and the organic layer was separated and washed with water and dehydrated over anhydrous sodium sulfate and the solvent was distilled off to obtain viscous liquid. This viscous liquid was crystallized and the crystal was washed with n-hexane to obtain 0.25 g. of the object compound (yield of 54%).

Workup

  1. additionof a solution containing 0.11 g
  2. temperaturethe mixture was refluxed for 12 hours
  3. customAfter the reaction, 10 ml
  4. customthe organic layer was separated
  5. washwashed with water
  6. distillationthe solvent was distilled off
  7. customto obtain viscous liquid
  8. customThis viscous liquid was crystallized
  9. washthe crystal was washed with n-hexane
  10. customto obtain 0.25 g

Sources & evidence

ORD record
ord-a7098fbf1175492fa06e2064b73db31a
Source dataset
uspto-grants-1994_11
Patent number
US05364831

Reaction notes

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