2,2'-Bipyridine → HCID 20427189, compound

HRID 544190Notes

Reaction equation

HRID 544190 reaction equation
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.N1C=CC=CC=1C1C=CC=CN=1.C([Li])CCC.[F:25][C:26]([F:46])([F:45])[C:27]1[CH:44]=[CH:43][C:30]([O:31][C:32]2[CH:42]=[CH:41][C:35]([O:36][CH2:37][C:38](Cl)=[O:39])=[CH:34][CH:33]=2)=[CH:29][CH:28]=1>CCCCCC.O.CCOCC.C1COCC1>[F:25][C:26]([F:45])([F:46])[C:27]1[CH:44]=[CH:43][C:30]([O:31][C:32]2[CH:42]=[CH:41][C:35]([O:36][CH2:37][C:38]([CH:2]3[C:3](=[O:6])[CH2:4][CH2:5][C:1]3=[O:7])=[O:39])=[CH:34][CH:33]=2)=[CH:29][CH:28]=1

Participants

9

Reactant 4

HCID 14742,2'-BipyridineHCID 774661,3-CyclopentanedioneHCID 20427191HCID 20427191, compoundHCID 178418339Butyllithium

Product 1

HCID 20427189HCID 20427189, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To THF (250 ml) under N2 with stirring is added cyclopentane-1,3-dione (0.10 mol) and 2,2'-bipyridyl (~3-5 mg) as an indicator. After cooling to -70°, n-butyllithium in hexane is added slowly while the temperature is allowed to rise to -5° near the end of the addition (~130 ml of 1.6 M solution, 0.20 mol). After the pink indicator persists at -5°, the mixture is recooled to -65° and 4-(4-trifluoromethylphenoxy)phenoxyacetyl chloride is added dropwise over 5 min. After 1 hour, the reaction mixture is diluted with water and ether is added. The organic layer is washed with water, dried over sodium sulfate and concentrated in vacuo to give 2-[4-(4-trifluoromethylphenoxy)phenoxyacetyl]cyclopentane-1,3-dione (V; Y is H, Z is CF3, R1 is H and n is one).

Workup

  1. temperatureAfter cooling to -70°
  2. customat -5°
  3. customis recooled to -65°
  4. additionis added
  5. washThe organic layer is washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f70bc4f5faf94216a3829c7c68518795
Source dataset
uspto-grants-1984_05
Patent number
US04448965

Reaction notes

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