Sodium Azide → HCID 86695687, compound

HRID 335331Notes

Reaction equation

HRID 335331 reaction equation
Br[CH2:2][CH:3]1[O:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4]1.[N-:10]=[N+:11]=[N-:12].[Na+]>CN(C=O)C>[N:10]([CH2:2][CH:3]1[O:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4]1)=[N+:11]=[N-:12]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 67034646123314-91-0

Product 1

HCID 86695687HCID 86695687, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5-(Bromomethyl)-2,2-dimethyltetrahydrofuran (36 g, 186 mmol) in DMF (300 ml) was treated with solid sodium azide (12.73 g, 196 mmol) and heated at 90° C. for 4 hrs. The mixture was allowed to cool to RT and partitioned between water (1.5 l) and ether (2×500 ml). The ether layer was separated and washed with (0.5M) LiCl (500 ml), dried MgSO4, filtered and evaporated to afford the title compound;

Workup

  1. temperatureto cool to RT
  2. custompartitioned between water (1.5 l) and ether (2×500 ml)
  3. customThe ether layer was separated
  4. washwashed with (0.5M) LiCl (500 ml), dried MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e9a2b5920acc401caf8824f69e2d5826
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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