Diethyl Ether → HCID 70983093, compound

HRID 339048Notes

Reaction equation

HRID 339048 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12]C(OC)=O)[N:8]=[C:7]([CH3:17])[CH:6]=[CH:5]2.[CH3:18][Mg+].[Br-].CC[O:23][CH2:24][CH3:25]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][C:24]([CH3:25])([OH:23])[CH3:18])[N:8]=[C:7]([CH3:17])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70983319HCID 70983319, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 70983093HCID 70983093, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of methyl 2-(6-fluoro-2-methylquinolin-7-yl)acetate (0.650 g, 2.79 mmol) in toluene (14 mL) was added dropwise a solution of MeMgBr in ether (3.0 M, 2.79 mL, 8.36 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at ambient temperature for 2 hours. The reaction was quenched by the addition of saturated aqueous NH4Cl solution. The reaction mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:2 hexanes/EtOAc) to give 1-(6-fluoro-2-methylquinolin-7-yl)-2-methylpropan-2-ol (0.202 g, 31%).

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous NH4Cl solution
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (1:2 hexanes/EtOAc)

Sources & evidence

ORD record
ord-db830e1426d14f14b6aebf833b334dd0
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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