N,N,N',N'-Tetramethylethylenediamine → HCID 178447841, compound

HRID 375782Notes

Reaction equation

HRID 375782 reaction equation
CN(CCN(C)C)C.[CH2:9]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)[CH2:10][CH3:11].[Li]CCCC.[O-]S(C(F)(F)[F:44])(=O)=O.F[N+]1C(C)=CC(C)=CC=1C>CCCCCC.C1COCC1>[CH2:9]([C@H:12]1[CH2:13][CH2:14][C@H:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[C:26]([F:44])[CH:25]=3)=[CH:20][CH:19]=2)[CH2:16][CH2:17]1)[CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 27245751-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]HCID 178418339ButyllithiumHCID 178447840HCID 178447840, compound

Product 1

HCID 178447841HCID 178447841, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

0.01 mol of TMEDA is added to a solution of 0.01 mol of 4-(trans-4-n-propylcyclohexyl)-4'-trifluoromethylbiphenyl in 10 ml of n-hexane. At 0°-5° C. 0.01 mol of n-BuLi is added, and stirring at RT is continued for another half an hour and at 40° C. for half an hour. The mixture is then cooled to 0° C., 20 ml of THF are added, and the fluorinating agent 1-fluoro-2,4,6-trimethylpyridinium triflate (in THF) is added dropwise at this temperature according to scheme 21. Extractive work-up and, as is customary, chromatography and crystallization give 4-(trans-4-n-propylcyclohexyl)-3'-fluoro-4'-trifluoromethylbiphenyl.

Workup

  1. customAt 0°-5° C
  2. waitis continued for another half an hour and at 40° C. for half an hour
  3. temperatureThe mixture is then cooled to 0° C.
  4. customchromatography and crystallization

Sources & evidence

ORD record
ord-6d83a9bcf640464d9ec979548bdf58e8
Source dataset
uspto-grants-1996_01
Patent number
US05487845

Reaction notes

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