N-Fluorobenzenesulfonimide → HCID 59739593, compound

HRID 1192968Notes

Reaction equation

HRID 1192968 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][N:5]=[C:4]([S:7]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])(=[O:9])=[O:8])[CH2:3]1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:29])(=O)=O)=CC=1>C1COCC1>[F:29][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([S:7]([C:4]1[CH2:3][C:2]([CH3:1])([CH3:18])[O:6][N:5]=1)(=[O:9])=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 588007N-FluorobenzenesulfonimideHCID 59739584HCID 59739584, compound

Product 1

HCID 59739593HCID 59739593, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phosphazene base 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda5-5,4-lambda5-5-catenadi(phosphazene) (P2-tBu) (2M in THF) (0.3 ml, 0.6 mmol) was added to a solution of 5,5-dimethyl-3-(1-phenyl-ethanesulfonyl)-4,5-dihydroisoxazole (150 mg, 0.56 mmol) in THF (8 ml) at room temperature. After 10 minutes N-fluorobenzene-sulfonimide (NFSI) (190 mg, 0.6 mmol) was added. The mixture was stirred at room temperature for 15 minutes. The mixture was absorbed onto silica gel and purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (Compound No. 1.138 of Table 27) as a white solid (89 mg, yield 56%).

Workup

  1. customThe mixture was absorbed onto silica gel
  2. custompurified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f1de8b014ff14afd9862bdd96a725109
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

Loading…