Diethyl Ether → HCID 70984215, compound

HRID 339041Notes

Reaction equation

HRID 339041 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5](C(OC)=O)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:16][Mg+].[Br-].CC[O:21][CH2:22][CH3:23]>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:22]([OH:21])([CH3:23])[CH3:16])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70984516HCID 70984516, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 70984215HCID 70984215, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a stirred solution of methyl 2-methylquinoline-8-carboxylate (0.290 g, 1.44 mmol) in THF (1 mL) was added dropwise a solution of MeMgBr in ether (3.0 M, 1.44 mL, 4.32 mmol) at −15° C. under nitrogen. The reaction mixture was stirred at −15° C. for 30 minutes and then 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 (1:1 hexanes/EtOAc) to give 2-(2-methylquinolin-8-yl)propan-2-ol (0.260 g, 90%).

Workup

  1. customquenched 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 (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-384b1df824e74f038f2e553a279a9c1e
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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