Methyl triflate → HCID 22463489, compound

HRID 1937120Notes

Reaction equation

HRID 1937120 reaction equation
[CH3:1]OS(C(F)(F)F)(=O)=O.[C:10]([C:17]1NC=CN=1)([C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)=[O:11].C(O)[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]>[N+](C)([O-])=O>[CH2:17]([C:10]([C:12]1[N:16]([CH3:1])[CH:15]=[CH:14][N:13]=1)=[O:11])[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]

Participants

5

Reactant 3

HCID 9526Methyl triflateHCID 68490alpha-HydroxyacetophenoneHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 22463489HCID 22463489, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Methyltriflate (1 mL, 8.84 mmol) was added dropwise to a solution of (0.959 g, 5.92 mmol) carbonyl diimidazole dissolved in 20 ml nitromethane. The solution was kept at about 0° C. during the addition. The solution was then warmed to room temperature and was allowed to stir for 1 h. The solution was then transferred to a flask containing freshly azeotroped (from benzene) 0.647 g (5.303 mmol) phenacyl alcohol. The resulting mixture was allowed to stir for 2 h at room temperature to form the phenacyl carbonyl-N-methylimidazole (not isolated or characterized). Freshly azotroped isopropyl alcohol (5.92 mmol) was then added and the reaction mixture was stirred overnight. The solvent was removed by vacuum distillation and the product was purified using silica gel flash chromatography with 80% hexane and 20% ethyl acetate. Yield 1.032 g (88%) from 0.715 g phenacyl alcohol, yellow oil; 1H NMR (CDCl3, 400 MHz) δ3.87 (s, 3H), 5.37 (s, 2H), 7.46-7.62 (m, 3H), 7.92 (d, J=6, 2H); 13C NMR (CDCl3, 110 MHz) δ191.9, 154.2, 133.8, 128.7, 127.5, 72.6, 68.2, 21.5; EI-MS, m/z (rel. intensity) 222 (M+, 1), 163 (27), 118 (32), 105 (100), 91 (60), 77 (66), 65 (13), 50 (44).

Workup

  1. additionThe solution was kept at about 0° C. during the addition
  2. customThe solution was then transferred to a flask
  3. additioncontaining freshly
  4. stirringto stir for 2 h at room temperature

Sources & evidence

ORD record
ord-4edb99aa8121475a8344aa74fd81189d
Source dataset
uspto-grants-2002_05
Patent number
US06392089B1

Reaction notes

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