2-Methyl-3-butyn-2-ol → HCID 86729354, compound

HRID 521187Notes

Reaction equation

HRID 521187 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+].[CH3:14][C:15]([OH:19])([C:17]#[CH:18])[CH3:16].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CS(C)=O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][N:10]1[CH:18]=[C:17]([C:15]([OH:19])([CH3:16])[CH3:14])[N:12]=[N:11]1

Participants

8

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 33557Sodium AzideHCID 699793-Bromobenzyl bromideHCID 23667548Sodium Ascorbate

Product 1

HCID 86729354HCID 86729354, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent4×

Procedure

To a solution of 1-bromo-3-(bromomethyl)benzene (5.0 g, 20 mmol) in DMSO (40 mL) was added sodium azide (1.3 g, 20 mmol). The resulting mixture was allowed to stir at ambient temperature for 18 hours before it was diluted with water and extracted with diethyl ether (2×). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was dissolved in tBuOH (65 mL and water (39 mL) and to this mixture was added 2-methylbut-3-yn-2-ol (2.3 g, 27 mmol), and then a solution of copper (II) sulfate pentahydrate (0.26 g, 1.0 mmol) in water (10 mL) followed by a solution of sodium ascorbate (0.83 g, 4.2 mmol) in water (8 mL). The resulting mixture was allowed to stir at ambient temperature for 2 hours before it was diluted with water and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was used without further purification.

Workup

  1. extractionextracted with diethyl ether (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude residue was dissolved in tBuOH (65 mL and water (39 mL)
  7. stirringto stir at ambient temperature for 2 hours before it
  8. extractionextracted with EtOAc (2×)
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was used without further purification

Sources & evidence

ORD record
ord-0e740d2f93b847c0a224e383f3379aa5
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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