Triphenylphosphine → 2-but-3-ynyl-2H-benzo[d][1,2,3]triazole

HRID 422344Notes

Reaction equation

HRID 422344 reaction equation
CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.[NH:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1.[CH2:26](O)[CH2:27][C:28]#[CH:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:29]([N:18]1[N:19]=[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]2=[N:17]1)[CH2:28][C:27]#[CH:26]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 135663-Butyn-1-OLHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 178418385HCID 178418385, compound

Product 1

HCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazoleYield 222%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of di-tert-butylazodicarboxylate (3.15 g, 13.4 mmol) in DCM (3 mL) was added dropwise over 30 min at 0° C. to a suspension of benzotriazole (2.40 g, 1.50 mmol), but-3-yn-1-ol (940 mg, 13.4 mmol) and polymer bounded triphenylphosphine (4.40 g, 16.8 mmol, 0.3 mmol/g) in DCM (3 mL). The reaction mixture was stirred at room temperature with a polymix agitation for 2 days and filtered through celite. The organic phase was washed with NH4OH, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1) to yield 571 mg (3.33 mmol, 25%) of 2-(but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a yellow solid.

Workup

  1. filtrationfiltered through celite
  2. washThe organic phase was washed with NH4OH, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1)

Sources & evidence

ORD record
ord-32960283d092423d8bf1e667e05fb9cb
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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