Sodium Azide → HCID 11297974, compound

HRID 736997Notes

Reaction equation

HRID 736997 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[O:5]1[CH2:9][CH2:8][CH:7]([CH2:10]OS(C)(=O)=O)[CH2:6]1>CN(C=O)C.O>[N:1]([CH2:10][CH:7]1[CH2:8][CH2:9][O:5][CH2:6]1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonate

Product 1

HCID 11297974HCID 11297974, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Add sodium azide (1.5 g, 23 mmol, 1.5 equiv) to a solution of methanesulfonic acid tetrahydro-furan-3-ylmethyl ester (2.76 g, 15.3 mmol, 1 equiv) in anhydr DMF (10 mL). Heat the reaction mixture at 50° C. for 16 h. Dilute the reaction mixture with H2O (100 mL) and extract with Et2O (2×50 mL). Wash the combined organic layers with H2O (2×50 mL), dry (anhydr Na2SO4), and rotary evaporate (40° C.) to yield 1.20 g (61.6%) of 3-azidomethyl-tetrahydro-furan as a nearly-colorless liquid.

Workup

  1. extractionextract with Et2O (2×50 mL)
  2. washWash the combined organic layers with H2O (2×50 mL)
  3. dry with materialdry (anhydr Na2SO4)
  4. customrotary evaporate (40° C.)

Sources & evidence

ORD record
ord-2517ad33e7b949e2879c604afb9c9799
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…