N-Fluorobenzenesulfonimide → HCID 22175082, compound

HRID 1797020Notes

Reaction equation

HRID 1797020 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[Li]C(C)(C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:31])(=O)=O)=CC=1.CCCCCC.CC(C)=O>CCOCC.C1COCC1>[F:31][C:13]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[O:7][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1]

Participants

7

Reactant 4

HCID 588007N-FluorobenzenesulfonimideHCID 15635484HCID 15635484, compoundHCID 21880519Acetone hexaneHCID 178418306HCID 178418306, compound

Product 1

HCID 22175082HCID 22175082, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 9 (12.39 g, 0.055 mol) in ether (200 mL) cooled to ≦−70° C. under an atmosphere of argon was slowly added t-BuLi (40 mL, 1.5 M pentane solution). During the addition, the reaction temperature was maintained at ≦−68° C. After the addition was complete the mixture was stirred an additional 60 minutes at ≦−70° C., then transferred via cannula to a stirred solution of N-fluorobenzenesulfonimide (18.92 g) in dry THF (200 mL) which was also cooled to ≦−70° C. under argon. After the addition was complete, the cooling bath was removed and the reaction mixture was allowed to warm up to room temperature. Water (100 mL) was added and the organic phase was separated, dried (MgSO4) and concentrated to give a brown oil. Chromatography (silica gel, hexane-acetone, 9:1) gave the desired product 10 as an orange oil (7.5 g) which contained about 15% starting material. This crude mixture was used directly in the next reaction.

Workup

  1. additionDuring the addition
  2. temperaturethe reaction temperature was maintained at ≦−68° C
  3. additionAfter the addition
  4. temperaturewas also cooled to ≦−70° C. under argon
  5. additionAfter the addition
  6. customthe cooling bath was removed
  7. additionWater (100 mL) was added
  8. customthe organic phase was separated
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a brown oil

Sources & evidence

ORD record
ord-0602a33a4fa746b5b5ffb74b78f7b7f3
Source dataset
uspto-grants-2006_04
Patent number
US07034035B2

Reaction notes

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