Lithium Chloride → 2-(Trimethylsilyl)ethyl 2-(2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxo-propyl)phenyl)butanoate

HRID 342007Notes

Reaction equation

HRID 342007 reaction equation
[Li+].[Cl-].[Li]OC(C)=O.[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH:19]=[CH:20][C:21]3[CH:22]=[C:23]([CH:27]([OH:30])[CH:28]=[CH2:29])[CH:24]=[CH:25][CH:26]=3)=[N:16]2)=[CH:11][CH:10]=1.I[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]([CH2:48][CH3:49])[C:39]([O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])=[O:40]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH:19]=[CH:20][C:21]3[CH:22]=[C:23]([C:27](=[O:30])[CH2:28][CH2:29][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[CH:38]([CH2:48][CH3:49])[C:39]([O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:47])[CH3:46])=[O:40])[CH:24]=[CH:25][CH:26]=3)=[N:16]2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 433294Lithium ChlorideHCID 534062851-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-olHCID 539675962-(Trimethylsilyl)ethyl 2-(2-iodophenyl)butanoateHCID 178506943lithium acetate

Product 1

HCID 536502412-(Trimethylsilyl)ethyl 2-(2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxo-propyl)phenyl)butanoateYield 83.1%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of LiCl (3.26 g, 77 mmol), LiOAc (19.6 g, 192 mmol), n-Bu4NCl (42.7 g, 154 mmol), Pd (OAc)2 (0.52 g, 2.3 mmol) and the allyl alcohol of Example 80, Step 1 (24.7 g, 77 mmol) under N2 was added a solution of the aryl iodide of Step 2 (30.0 g, 77 mmol) in DMF (150 mL). The suspension was degassed and purged with N2, and was then stirred at 100° C. for 1 h. The dark red solution was then poured onto a mixture of ice (300 g) and saturated NaHCO3 (300 mL). The red syrup was extracted with EtOAc. Following filtration through celite, the organic phase was washed with H2O and saturated NaCl solution. After drying (MgSO4), the solvent was removed under vacuum and the residue was purified by flash chromatography. Elution was effected with 1:20 EtOAc:hexane, followed by 1:10 EtOAc:hexane to give 37.4 g of the title compound as a white solid, mp 109°-111° C.

Workup

  1. customThe suspension was degassed
  2. custompurged with N2
  3. additionThe dark red solution was then poured onto a mixture of ice (300 g) and saturated NaHCO3 (300 mL)
  4. extractionThe red syrup was extracted with EtOAc
  5. filtrationfiltration through celite
  6. washthe organic phase was washed with H2O and saturated NaCl solution
  7. dry with materialAfter drying (MgSO4)
  8. customthe solvent was removed under vacuum
  9. customthe residue was purified by flash chromatography
  10. washElution

Sources & evidence

ORD record
ord-ea372fbe6d21465aadaab19c51bda4b7
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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