N,N,N',N'-Tetramethylethylenediamine → HCID 178447957, compound

HRID 2268104Notes

Reaction equation

HRID 2268104 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].CN(CCN(C)C)C.[Li]CCCC.[Cl:40]N1C(=O)CCC1=O>C1COCC1.C(OCC)C.O>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[C:19]2[CH:20]=[C:21]([F:26])[C:22]([Cl:40])=[C:23]([F:25])[CH:24]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 31398ChlorosuccinimideHCID 178418339ButyllithiumHCID 178447956HCID 178447956, compound

Product 1

HCID 178447957HCID 178447957, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.1 m of 1-(trans-4-n-propylcyclo-hexyl)-2-(3,3′, 5′-trifluorobiphenylyl)ethane and 0.1 m of TMEDA in 300 ml of THF is treated dropwise at about -65° with 0.1 m of n-BuLi (1.5 M in hexane). The mixture is stirred at this temperature for a further 30 minutes, and 0.2 m of N-chlorosuccinimide in 70 ml of THF is then slowly added. When the addition is complete, the mixture is allowed to warm to −20° and is hydrolyzed using H2O. The product is dissolved completely by adding diethyl ether. Extractive work-up and purification by chromatography and crystallization give l-(trans-4-n-propylcyclohexyl)-2-(4′-chloro-3,3′, 5′-trifluorobiphenylyl)ethane.

Workup

  1. additionWhen the addition
  2. temperatureto warm to −20°
  3. dissolutionThe product is dissolved completely
  4. customExtractive work-up and purification
  5. customby chromatography and crystallization

Sources & evidence

ORD record
ord-6ca0bc0beb764b12ad6eb69bf317b47c
Source dataset
uspto-grants-2001_12
Patent number
US06326066B1

Reaction notes

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