Chlorotrimethylsilane → Ethyl 3-methyl-3-(2-methylquinolin-8-yl)butanoate

HRID 339038Notes

Reaction equation

HRID 339038 reaction equation
[Li][CH3:2].C[Si](Cl)(C)C.[CH3:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[C:12](/[C:19](/[CH3:26])=[CH:20]\[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:13]=[CH:14][CH:15]=2)[N:10]=1>CCOCC.C(Cl)Cl>[CH3:26][C:19]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[N:10]=[C:9]([CH3:8])[CH:18]=[CH:17]2)([CH3:2])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 70983529(Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoateHCID 178418348HCID 178418348, compound

Product 1

HCID 70984548Ethyl 3-methyl-3-(2-methylquinolin-8-yl)butanoateYield 76.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of Cu(I)I (2.42 g, 12.7 mmol) in ether (5 mL) was added a solution of 1.6 M MeLi (15.9 ml, 25.4 mmol) in ether at 0° C. and the mixture was stirred at 0° C. for 10 minutes. The solvent was removed under reduced pressure and cold DCM (10 mL) was added. The solvent was removed under reduced pressure. Cold DCM (40 mL) was added and the mixture was cooled to −78° C. TMSCl (1.54 mL, 12.7 mmol) was added, followed by a solution of (Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoate (0.81 g, 3.17 mmol) in DCM (10 mL). The reaction mixture was warmed to 0° C. and stirred at 0° C. for 1 hour. The reaction mixture was quenched with saturated ammonium chloride solution. The organic layers was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (7:1 hexane/ethyl acetate) to give ethyl 3-methyl-3-(2-methylquinolin-8-yl)butanoate (0.66 g, 76.8%) as an oil.

Workup

  1. customThe solvent was removed under reduced pressure and cold DCM (10 mL)
  2. additionwas added
  3. customThe solvent was removed under reduced pressure
  4. additionCold DCM (40 mL) was added
  5. temperaturethe mixture was cooled to −78° C
  6. temperatureThe reaction mixture was warmed to 0° C.
  7. stirringstirred at 0° C. for 1 hour
  8. customThe reaction mixture was quenched with saturated ammonium chloride solution
  9. customThe organic layers was separated
  10. washwashed with brine
  11. dry with materialdried (sodium sulfate)
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by flash chromatography on silica gel (7:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-55b88b37eeb64b3bbff75d0f0ece3621
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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