Tetrahydrofuran → HCID 87106287, compound

HRID 922307Notes

Reaction equation

HRID 922307 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)\[CH2:5][O:6][C:7]1[CH:27]=[CH:26][C:10]([CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.C1COCC1.[OH-].[Na+]>C(O)C>[CH3:1][O:2]/[N:3]=[C:4](/[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)\[CH2:5][O:6][C:7]1[CH:27]=[CH:26][C:10]([CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 87106032HCID 87106032, compound

Product 1

HCID 87106287HCID 87106287, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of ethyl 3-{6-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]pyridin-3-yl}propanoate (0.03 g, 0.067 mmol) in the mixture of THF and Ethanol was added aqueous NaOH (0.03 g, 0.067 mmol) at 0° C., then stirred at RT for 2 h. After the completion of the SM reaction mass was concentrated under vacuum at 25° C. to remove solvents and diluted with water. Aqueous portion was neutralized with citric acid up to neutral pH, then extracted with ethyl acetate organic layer was washed with water and brine, dried over Na2SO4 and concentrated. Crude product was purified by preparative TLC to afford colourless oil as product (0.01 g, Yield: 35%); purity: 85%.

Workup

  1. customAfter the completion of the SM reaction mass
  2. concentrationwas concentrated under vacuum at 25° C.
  3. customto remove solvents
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate organic layer
  6. washwas washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customCrude product was purified by preparative TLC
  10. customto afford colourless oil as product (0.01 g, Yield: 35%)

Sources & evidence

ORD record
ord-d852865eb2d2430f80ba445caa5bbb3c
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

Loading…