Water → HCID 68527299, compound

HRID 1932449Notes

Reaction equation

HRID 1932449 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19](O)=[O:20])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].B.C1COCC1.O>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][OH:20])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 68523165HCID 68523165, compound

Product 1

HCID 68527299HCID 68527299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[4-(5-nitropyridin-2-yloxy)phenyl]propionic acid (2.64 g, 9.2 mmol) in THF (50 mL) was added dropwise a 1 M borane-THF complex THF solution (38.4 mL, 38.4 mmol) under ice cooling. The reaction solution was stirred for 2 hours at room temperature. Water was added to the reaction mixture, and extracted with ethyl acetate, and the ethyl acetate layer was washed with water and then brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, after which solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to thereby yield 1.17 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe ethyl acetate layer was washed with water
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. customafter which solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-04acfcbf1f654d05b54356b29d05b3d9
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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