2-Methyl-3-butyn-2-ol → HCID 59526350, compound

HRID 386116Notes

Reaction equation

HRID 386116 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:9][C:10]([OH:14])([C:12]#[CH:13])[CH3:11].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:13]#[C:12][C:10]([CH3:11])([OH:14])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 673313,6-Dichloropyridazine

Product 1

HCID 59526350HCID 59526350, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,6-dichloropyridazine (250 mg, 1.68 mmol) and 2-methylbut-3-yn-2-ol (282 mg, 3.36 mmol) in DMF (4 mL) were added CuI (64 mg, 0.33 mmol), triethylamine (0.47 mL, 3.36 mmol), and palladium tetrakis triphenylphosphine (194, 0.168 mmol). The solution was degassed and heated to 80° C. overnight. The residue was worked up with EtOAc and water, dried with MgSO4, filtered, and concentrated. Column chromatography on silica gel 100% Hex to 100% EtOAc provided the title compound.

Workup

  1. customThe solution was degassed
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3b8b45aa30624347b51a7afcd576436e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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