(Diethylamino)sulfur trifluoride → HCID 178439342, compound

HRID 2392505Notes

Reaction equation

HRID 2392505 reaction equation
C(N(S(F)(F)[F:7])CC)C.[F:10][C:11]1[CH:16]=[C:15]([CH2:17][CH2:18][CH3:19])[CH:14]=[C:13]([F:20])[C:12]=1[CH2:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH:29]2[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]2)[CH2:25][CH2:24]1>C(COC)OC.FC(F)(F)S(O)(=O)=O>[F:7][C:32]1[CH2:33][CH2:34][CH:29]([C@H:26]2[CH2:27][CH2:28][C@H:23]([CH2:22][CH2:21][C:12]3[C:11]([F:10])=[CH:16][C:15]([CH2:17][CH2:18][CH3:19])=[CH:14][C:13]=3[F:20])[CH2:24][CH2:25]2)[CH2:30][CH:31]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 178439343HCID 178439343, compound

Product 1

HCID 178439342HCID 178439342, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

1.1 ml of diethylaminosulphur trifluoride (DAST) are added dropwise in 3 portions over 60 hours to a solution of 1.7 g of 4-{trans-4-[2-(2,6-difluoro-4-propylphenyl)ethyl]cyclohexyl}cyclohexanone in 30 ml of dimethoxyethane and 0.1 ml of trifluoro-methanesulphonic acid. The reaction solution is subsequently partitioned between sodium carbonate solution/ether. The organic phase is washed twice with water and the aqueous phases are individually extracted twice with ether. The organic phases are combined, dried over magnesium sulfate, filtered and the filtrate is evaporated completely. The crude product obtained is chromatographed over silica gel and gives 1-fluoro-4-{trans-4-[2-(2,6-difluoro-4-propylphenyl)ethyl]cyclohexyl }cyclohex-1-ene.

Workup

  1. customThe reaction solution is subsequently partitioned between sodium carbonate solution/ether
  2. washThe organic phase is washed twice with water
  3. extractionthe aqueous phases are individually extracted twice with ether
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate is evaporated completely
  7. customThe crude product obtained
  8. customis chromatographed over silica gel

Sources & evidence

ORD record
ord-4f4ff5042b28411a8a5616972f99a53b
Source dataset
uspto-grants-1998_09
Patent number
US05800734

Reaction notes

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