Cesium carbonate → HCID 70983350, compound

HRID 339060

Reaction equation

HRID 339060 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:19][C@@H:20]1[CH2:22][O:21]1>CN(C=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH2:19][C@H:20]([OH:21])[CH3:22])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146261(R)-1,2-EpoxypropaneHCID 1354519692-Methylquinolin-7-ol

Product 1

HCID 70983350HCID 70983350, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of 2-methylquinolin-7-ol (0.400 g, 2.51 mmol), Cs2CO3 (2.46 g, 7.54 mmol) and DMF (16 mL) was added (R)-2-methyloxirane (0.438 g, 7.54 mmol). The reaction mixture was heated at 80° C. for 2 hours. After cooling, the reaction mixture was partitioned between ether and water. The aqueous layer was extracted with ether. The combined organic layers were washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1% MeOH in EtOAc) to give (R)-1-(2-methylquinolin-7-yloxy)propan-2-ol (0.471 g, 86%).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ether and water
  3. extractionThe aqueous layer was extracted with ether
  4. washThe combined organic layers were washed with water and brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (1% MeOH in EtOAc)

Sources & evidence

ORD record
ord-4cacfb806efe4aa98b1b3a01bd7d411c
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Linked notes

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