Potassium Carbonate → 4-(Ethylsulfanyl)-2,2,3,3-tetramethyl-2,3-dihydroazete

HRID 1534005Notes

Reaction equation

HRID 1534005 reaction equation
F[B-](F)(F)F.[CH2:6]([O+](CC)CC)[CH3:7].[CH3:13][C:14]1([CH3:21])[NH:17][C:16](=[S:18])[C:15]1([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:6]([S:18][C:16]1[C:15]([CH3:20])([CH3:19])[C:14]([CH3:21])([CH3:13])[N:17]=1)[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723982Triethyloxonium tetrafluoroborateHCID 19911807HCID 19911807, compound

Product 1

HCID 144723344-(Ethylsulfanyl)-2,2,3,3-tetramethyl-2,3-dihydroazete

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10.5 ml of triethyloxonium tetrafluoroborate as a 1M solution in CH2Cl2, a solution of 1 g (7 mmol) of tetramethylazetidinethione in 3 ml of dry CH2Cl2 was added under an inert atmosphere. The mixture was stirred at room temperature for 1 hour and then reflux for 1 hour. After cooling, it was added dropwise to 10 mol of a 50% K2CO3 solution at -10° C. After filtration, the organic phase was separated out and immediately dried over MgSO4. Filtration was followed by removal of the solvent under vacuum and the oily residue was subjected to flash silica chromatography (pet. ether : ethyl acetate ; 8:2) to obtain the product as a colorless oil.

Workup

  1. temperaturereflux for 1 hour
  2. temperatureAfter cooling
  3. filtrationAfter filtration
  4. customthe organic phase was separated out
  5. dry with materialimmediately dried over MgSO4
  6. filtrationFiltration
  7. customwas followed by removal of the solvent under vacuum

Sources & evidence

ORD record
ord-55d18a17d9fa4f6d8b8421dd36768904
Source dataset
uspto-grants-1992_02
Patent number
US05086170

Reaction notes

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