Sodium Azide → HCID 178459231, compound

HRID 2368134Notes

Reaction equation

HRID 2368134 reaction equation
CS(O[CH:6]([CH3:29])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[O:16][C:17]3[CH:23]=[C:22]([O:24][CH2:25][CH:26]4[CH2:28][CH2:27]4)[CH:21]=[CH:20][C:18]=3[CH:19]=2)[CH2:11][CH2:10]1)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C=O)C>[N:30]([CH:6]([CH3:29])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[O:16][C:17]3[CH:23]=[C:22]([O:24][CH2:25][CH:26]4[CH2:28][CH2:27]4)[CH:21]=[CH:20][C:18]=3[CH:19]=2)[CH2:11][CH2:10]1)=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178459232HCID 178459232, compound

Product 1

HCID 178459231HCID 178459231, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2-({trans-4-[6-(cyclopropylmethoxy)-1-benzofuran-2-yl]cyclohexyl}oxy)-1-methylethyl methanesulfonate 624 mg) and sodium azide (480 mg) in DMF (5 mL) was stirred at 60° C. overnight. The reaction mixture was allowed to cool to room temperature, and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (397 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate and water
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-751ab8822ed040d8b6c2d4145f9e27a8
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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