Cornforth reagent → HCID 178519382, compound

HRID 1615195Notes

Reaction equation

HRID 1615195 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][OH:11])=[CH:9][C:4]=2[N:3]=[N:2]1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>CC(C)=O>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 178519383HCID 178519383, compound

Product 1

HCID 178519382HCID 178519382, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of (1H-benzo[d][1,2,3]triazol-5-yl)methanol (0.860 g, 5.77 mmol) in acetone (25 mL) was purged with Ar, by bubbling through solution, then PDC (2.60 g, 6.92 mmol) was added portion-wise over 20 min. The reaction was stirred overnight (18 hrs). The acetone was removed in vacuo, the solids dissolved in MeOH and silica gel was added. The MeOH was then removed and the silica dry-loaded onto a silica gel column, and the product eluted with 1:1 Hexanes/EtOAc to give 444 mg, 52% of a white solid. 1H NMR (400 MHz, CD3OD) δ 10.14 (s, 1H), 8.55 (s, 1H), 8.04 (d, J=8.8 Hz, 1H), 7.96 (d, J=8.4 Hz, 1H); MS ESI 148.0 [M+H]+, calcd for [C7H5N3O+H]+ 148.14.

Workup

  1. customwas purged with Ar
  2. customby bubbling through solution
  3. customThe acetone was removed in vacuo
  4. dissolutionthe solids dissolved in MeOH
  5. additionsilica gel was added
  6. customThe MeOH was then removed
  7. washthe silica dry-loaded onto a silica gel column, and the product eluted with 1:1 Hexanes/EtOAc

Sources & evidence

ORD record
ord-8df70d407ce24b65a129b39173c0f737
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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