(Diethylamino)sulfur trifluoride → HCID 18979657, compound

HRID 2392504Notes

Reaction equation

HRID 2392504 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[CH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1>C(COC)OC.FC(F)(F)S(O)(=O)=O>[F:7][C:24]1[CH2:25][CH2:26][CH:21]([C:12]2[C:11]([F:10])=[CH:16][C:15]([CH2:17][CH2:18][CH3:19])=[CH:14][C:13]=2[F:20])[CH2:22][CH:23]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 18979645HCID 18979645, compound

Product 1

HCID 18979657HCID 18979657, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

535 ml of diethylaminosulphur trifluoride (DAST) were added dropwise in 3 portions over 60 hours to a solution of 0.63 g of 4-(2,6-difluoro-4-propylphenyl)cyclohexanone in 15 ml of dimethoxyethane and 50 ml of trifluoromethanesulphonic acid. The reaction solution was subsequently partitioned between sodium carbonate solution and ether. The organic phase was washed twice with water and the aqueous phases were individually extracted twice with ether. The organic phases were combined, dried over magnesium sulfate, filtered and the filtrate was evaporated completely. The resulting crude product (0.8 g) was purified by chromatography and gave 0.36 g of 1-fluoro-4-(2,6-difluoro-4-propylphenyl)cyclohex-1-ene, m.p. (C/I) 62.5° C.

Workup

  1. customThe reaction solution was subsequently partitioned between sodium carbonate solution and ether
  2. washThe organic phase was washed twice with water
  3. extractionthe aqueous phases were individually extracted twice with ether
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated completely
  7. customThe resulting crude product (0.8 g) was purified by chromatography

Sources & evidence

ORD record
ord-fb6eaf8662514b599e06ff953ebdaac3
Source dataset
uspto-grants-1998_09
Patent number
US05800734

Reaction notes

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