Tetrahydrofuran → HCID 22636759, compound

HRID 2415780Notes

Reaction equation

HRID 2415780 reaction equation
[N+]([CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([O-])=O.[CH:12]([O-:14])=O.[NH4+:15].[H][H].C1C[O:21][CH2:20][CH2:19]1>CO.[Pd]>[NH2:15][C:7]1[CH:6]=[C:5]([CH2:4][OH:11])[C:10]2[O:14][CH2:12][CH2:19][CH2:20][O:21][C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 21879777Nitrobenzyl alcoholHCID 178418361HCID 178418361, compound

Product 1

HCID 22636759HCID 22636759, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.25 g (0.01 mol) of nitro benzyl alcohol compound was dissolved in a mixture of 45 mL of methanol and 45 mL of THF. A solid ammonium formate was then added (3.18 g, 0.05 mol, 5 equivalents) followed by the careful addition of 455 mg of 10% palladium on carbon. The reaction mixture was then stirred very slowly at room temperature under reflux condenser. Once it starts, the reaction was rapid and exothermic. After about 1 hour the evolution of hydrogen gas ceased and reaction was checked on TLC (more polar product formation, reaction was dome after this time). The crude reaction was then filtered thru celite, the filtrate diluted with four times of its volume of diethyl ether. The white precipitate that formed was filtered off and dried in vacuo. 1.403 g (72%) of off-white solid was collected.

Workup

  1. temperatureunder reflux condenser
  2. customreaction
  3. custommore polar product formation, reaction
  4. customThe crude reaction
  5. filtrationwas then filtered thru celite
  6. additionthe filtrate diluted with four times of its volume of diethyl ether
  7. customThe white precipitate that formed
  8. filtrationwas filtered off
  9. customdried in vacuo
  10. custom1.403 g (72%) of off-white solid was collected

Sources & evidence

ORD record
ord-1adc7887ea194dbb845d26a56dfd905a
Source dataset
uspto-grants-2004_11
Patent number
US06821977B2

Reaction notes

Loading…