Water → HCID 131729983, compound

HRID 2061608Notes

Reaction equation

HRID 2061608 reaction equation
[Cl-].[OH:2][C:3]1[C:4]([CH3:18])=[N+:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1.FC(F)(F)S(O[C:25]1[CH:30]=[CH:29]C=[CH:27][C:26]=1[Si](C)(C)C)(=O)=O.[F-].[Cs+].O.[CH3:40]C#N>>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:5]2[CH:6]3[C:29]4[CH:30]=[CH:25][CH:26]=[CH:27][C:18]=4[C:4]2([CH3:40])[C:3](=[O:2])[CH:8]=[CH:7]3)=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 25953Cesium fluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonateHCID 67303374HCID 67303374, compound

Product 1

HCID 131729983HCID 131729983, compound

Procedure

To a suspension of compound 73 (11.97 g) in CH3CN (125 mL) was added 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (75) (30 g) and CsF (20 g). The mixture was stirred at room temperature for 3 days. Water was added to quench the reaction and most of the CH3CN was removed via rotavaporator. The residue was extracted with EtOAc, washed with water and brine, and dried over MgSO4. After concentration of the solvent, the crude product was purified by silica gel chromatography, eluting with a gradient of 100% hexane to 80% EtOAc/hexane over 30 min. The pure product was isolated as a brown oil. 1H NMR (CDCl3) δ 7.30-7.24 (m 3H), 7.21-7.15 (m, 3H), 7.01 (dd, 1H, J=5.1, 9.6 Hz), 6.87 (d, 2H, J=8.7 Hz), 5.62 (d, 2H, J=9.6 Hz), 4.31 (d, 1H, J=5.1 Hz), 3.81 (s 3H), 1.65 (s, 3H).

Workup

  1. customto quench
  2. customthe reaction
  3. custommost of the CH3CN was removed via rotavaporator
  4. extractionThe residue was extracted with EtOAc
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customAfter concentration of the solvent, the crude product was purified by silica gel chromatography
  8. washeluting with a gradient of 100% hexane to 80% EtOAc/hexane over 30 min
  9. customThe pure product was isolated as a brown oil

Sources & evidence

ORD record
ord-d5edf233a032431ab747b696e11a229a
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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