HCID 89525383, compound → 1432041-34-3

HRID 1050968Notes

Reaction equation

HRID 1050968 reaction equation
[N:1]([CH:4]([C:11]1([CH3:16])[CH2:15][CH2:14][CH2:13][O:12]1)[C:5]1[O:6][C:7]([CH3:10])=[CH:8][CH:9]=1)=[N+]=[N-].[H][H]>C(O)C.[Pd]>[CH3:10][C:7]1[O:6][C:5]([CH:4]([C:11]2([CH3:16])[CH2:15][CH2:14][CH2:13][O:12]2)[NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 89525383HCID 89525383, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 801817901432041-34-3Yield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.51 g (9.7 mmol, 1 eq) of 2-[azido-(2-methyltetrahydrofuran-2-yl)methyl]-5-methylfuran in 45 ml of ethanol was stirred at hydrogen atmospheric pressure in the presence of 323 mg (15% by weight) of palladium on carbon (Pd/C) at 10% for 16 hours. The reaction medium was filtered and the filtrate was evaporated. 1.82 g of (5-methylfuran-2-yl)(2-methyltetrahydrofuran-2-yl)methanamine were obtained. Yield=96%. TLC/SiO2: heptane/EtOAc (60/40), developing with KMnO4.

Workup

  1. filtrationThe reaction medium was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e4136df696f747b3a2241ac8b3fec169
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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