Water → Methyl 1-(2-methylquinolin-8-yl)cyclopropanecarboxylate

HRID 338908Notes

Reaction equation

HRID 338908 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].Br[CH2:20][CH2:21]Cl.O>CS(C)=O.C1COCC1.CCOCC>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3([C:13]([O:15][CH3:16])=[O:14])[CH2:21][CH2:20]3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 70984092Methyl 2-(2-methylquinolin-8-yl)acetate

Product 1

HCID 70984245Methyl 1-(2-methylquinolin-8-yl)cyclopropanecarboxylateYield 47.6%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(2-methylquinolin-8-yl)acetate (0.78 g, 3.62 mmol) in DMSO (10 mL) and THF (5 mL) was added 60% NaH (0.72 g, 18.12 mmol) and the reaction mixture was stirred at ambient temperature for 30 minutes. 1-Bromo-2-chloroethane (0.90 mL, 10.87 mmol) was added slowly, and the reaction mixture was stirred at ambient temperature for 40 hours. Water (10 mL) and ether (50 mL) were added. The organic layer 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 methyl 1-(2-methylquinolin-8-yl)cyclopropanecarboxylate (0.416 g, 47.6%) as an oil.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 40 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (7:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d3057b49f7e0408a974652012d4c042f
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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