Pyridine → HCID 178454382, compound

HRID 1464833Notes

Reaction equation

HRID 1464833 reaction equation
[CH:1]1([Ti:6]([CH:25]2[CH:29]=[CH:28][CH:27]=[CH:26]2)([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=2[F:24])[C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([OH:14])[C:8]=2[F:15])[CH:5]=[CH:4][CH:3]=[CH:2]1.N1[CH:35]=[CH:34][CH:33]=CC=1.C1(C)C=CC=CC=1.Cl[C:44]([O:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[O:45].[C:51]([O:54][CH2:55]C)(=[O:53])C>CN(C)C1C=CC=CN=1.CN(C)C=O.O>[CH:25]1([Ti:6]([CH:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([O:14][C:51]([O:54][CH2:55][CH:34]([CH3:33])[CH3:35])=[O:53])[C:8]=2[F:15])[C:16]2[C:21]([F:22])=[CH:20][CH:19]=[C:18]([O:23][C:44]([O:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[O:45])[C:17]=2[F:24])[CH:29]=[CH:28][CH:27]=[CH:26]1

Participants

9

Reactant 5

HCID 1049PyridineHCID 1140TolueneHCID 8857Ethyl AcetateHCID 62365Isobutyl chloroformateHCID 178516123HCID 178516123, compound

Product 1

HCID 178454382HCID 178454382, compound

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8.7 g (0.020 mol) of bis(cyclopentadienyl)bis(2,6-difluoro-3-hydroxyphenyl)titanium, 3.8 g (0.048 mol) of pyridine and a small spatula tip of 2-dimethylaminopyridine as catalyst are dissolved in 20 ml of dimethylformamide and 30 ml of toluene in a 100 ml sulfation flask under nitrogen. 6.6 g (0.048 mol) of isobutyl chloroformate are added dropwise to this dark-red solution at room temperature over the course of 10 minutes. The reaction mixture is stirred overnight at room temperature until the educt no longer appears in the thin-layer chromatogram. The suspension is poured into 100 ml of ethyl acetate and 100 ml of water, and the mixture is stirred and filtered through Hyflo. The two phases of the filtrate are separated from one another. The organic phase is dried using magnesium sulfate, filtered and evaporated in a vacuum rotary evaporator at 20 mbar and a bath temperature of 40° C. A dark-red oil is obtained and is purified by flash chromatography using hexane/ethyl acetate (3:1) as solvent. 6.6 g (52% of theory) of an orange-red glassy resin are obtained.

Workup

  1. stirringthe mixture is stirred
  2. filtrationfiltered through Hyflo
  3. customThe two phases of the filtrate are separated from one another
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated in a vacuum rotary evaporator at 20 mbar and a bath temperature of 40° C
  7. customA dark-red oil is obtained
  8. customis purified by flash chromatography
  9. custom6.6 g (52% of theory) of an orange-red glassy resin are obtained

Sources & evidence

ORD record
ord-86395988b3df46d7866dfcc99df4f89b
Source dataset
uspto-grants-1994_04
Patent number
US05306600

Reaction notes

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