Water → HCID 89525383, compound

HRID 1050967Notes

Reaction equation

HRID 1050967 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:18][C:19]1[O:23][C:22]([CH:24]([C:26]2([CH3:31])[CH2:30][CH2:29][CH2:28][O:27]2)O)=[CH:21][CH:20]=1.N12CCCN=C1CCCCC2.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:15]([CH:24]([C:26]1([CH3:31])[CH2:30][CH2:29][CH2:28][O:27]1)[C:22]1[O:23][C:19]([CH3:18])=[CH:20][CH:21]=1)=[N+:16]=[N-:17]

Participants

7

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 89525540HCID 89525540, compound

Product 1

HCID 89525383HCID 89525383, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

8.77 g (31.8 mmol, 1.2 eq) of diphenylphosphoryl azide were added dropwise to a solution of 5.21 g (26.5 mmol, 1 eq) of (5-methylfuran-2-yl)-(2-methyltetrahydrofuran-2-yl)methanol in 90 ml of toluene. The reaction medium was cooled to 0° C. and then 4.75 ml (31.8 mmol, 1.2 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added dropwise. The reaction medium was stirred at ambient temperature for 41 hours. The (heterogeneous) reaction medium was treated with water and with ethyl acetate and then separated by settling out. The organic phase was washed with 1 N hydrochloric acid, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on HP silica gel (column puriFlash IR50SI-200G, Spot II) eluted with heptane/ethyl acetate (95/5). 2.15 g of 2-[azido-(2-methyltetrahydrofuran-2-yl)methyl]-5-methylfuran were obtained. Yield=37%. TLC/SiO2: heptane/EtOAc (80/20), developing with KMnO4.

Workup

  1. customThe (heterogeneous) reaction medium
  2. customseparated
  3. washThe organic phase was washed with 1 N hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on HP silica gel (column puriFlash IR50SI-200G, Spot II)
  8. washeluted with heptane/ethyl acetate (95/5)

Sources & evidence

ORD record
ord-d34e0fa97c834683829c3b6ea952f3b9
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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