N-Fluorobenzenesulfonimide → HCID 68524225, compound

HRID 2386190Notes

Reaction equation

HRID 2386190 reaction equation
[Si:1]([O:8][CH:9]([C:22]1[O:23][CH:24]=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]C(C)(C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:42])(=O)=O)=CC=1>C1COCC1.CCOC(C)=O>[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([F:42])=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 685237222-(1-{[tert-Butyl(dimethyl)silyl]oxy}-7-phenylheptyl)-1,3-oxazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 68524225HCID 68524225, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazole (135 mg, 0.361 mmol) was dissolved in anhydrous THF (5 mL), cooled to −78° C. and t-BuLi (1.7 M in pentane, 1.3 equiv) was added dropwise under Ar. The reaction mixture was stirred for 2 h at −40° C., and N-fluorobenzenesulfonimide (1.5 equiv) was added in one portion. The reaction mixture was warmed to room temperature, diluted with EtOAc, washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude aryl fluoride, which was purified by flash chromatography (0-2% EtOAc/hexanes) to afford the title compound as a clear oil (31 mg, 22%): 1H NMR (CDCl3, 500 MHz) 7.37-7.34 (m, 2H), 7.27-7.24 (m, 3H), 6.36 (d, 1H, J=9.0 Hz), 4.71 (t, 1H, J=7.2 Hz), 2.68 (t, 2H, J=7.8 Hz), 1.94-1.86 (m, 2H), 1.71-1.66 (m, 2H), 1.51-1.43 (m, 6H), 0.96 (s, 9H), 0.16 (s, 3H), 0.07 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 158.6 (d, J=292 Hz), 143.2, 128.8, 128.7, 126.0, 99.1 (d, J=12.8 Hz), 69.2, 36.4, 36.3, 31.8, 29.5, 29.5, 26.1, 25.4, 18.6, −4.7, −4.8.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. washwashed with saturated aqueous NaCl
  3. dry with materialdried over Na2SO4
  4. customEvaporation in vacuo
  5. customyielded the crude aryl fluoride, which
  6. customwas purified by flash chromatography (0-2% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e183ddc3e67047ad873af8270f44deef
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

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