Ammonium Chloride → HCID 87260512, compound

HRID 2088955Notes

Reaction equation

HRID 2088955 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:33])(=O)=O)=CC=1.[Cl-].[NH4+]>O1CCCC1.O>[F:33][CH:7]([CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 588007N-FluorobenzenesulfonimideHCID 2733832Lithium HexamethyldisilazideHCID 2773412Ethyl tetrahydropyran-4-ylacetate

Product 1

HCID 87260512HCID 87260512, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (2.0 g) was dissolved in tetrahydrofuran (20 ml). A solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1.0 M, 17 ml) was added dropwise under nitrogen atmosphere under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. Then, a solution of N-fluorobenzenesulfonimide (7.3 g) in tetrahydrofuran (20 ml) was added and the mixture was stirred at the same temperature for 3 hours. A saturated aqueous ammonium chloride solution and water were added under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated. Chloroform-diethyl ether was added to the residue, and insoluble matter was removed by filtration. Thereafter, the solvent was evaporated and the residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane and with chloroform) to give the title compound containing insoluble matter (0.9 g) as a pale orange oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 3 hours
  3. temperaturecooling
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. additionChloroform-diethyl ether was added to the residue, and insoluble matter
  9. customwas removed by filtration
  10. customThereafter, the solvent was evaporated
  11. customthe residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane and with chloroform)

Sources & evidence

ORD record
ord-4c266270683e4ecca897fe783fb8a2bc
Source dataset
uspto-grants-2013_05
Patent number
US08436012B2

Reaction notes

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