Sodium Azide → 7-Azido-1-heptanol

HRID 2097347Notes

Reaction equation

HRID 2097347 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]>CN(C=O)C>[N:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 662841-Heptanol, 7-bromo-

Product 1

HCID 231324227-Azido-1-heptanolYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

NaN3 (390 mg, 6.0 mmol) was added to a solution of 7-bromoheptanol (880 μL, 5.7 mmol) in DMF (5 mL). The mixture was stirred for 24 at r.t. and additional 3 h at 80° C. to complete the reaction. The mixture was concentrated under reduced pressure, the residue was dissolved in water/Et2O (10/20 mL), the organic layer was separated, dried over Na2SO4 and filtered. Concentration under reduced pressure yielded 7-azidoheptanol (710 mg, 78%) as an colourless oil which was pure enough for further reactions.

Workup

  1. customthe reaction
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water/Et2O (10/20 mL)
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-1f6be5fcaacb46758b1e08fcebe7dbe3
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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