2,6-Lutidine → HCID 89767711, compound

HRID 591574Notes

Reaction equation

HRID 591574 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:11]=[C:10]([O:12][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH:9]=[CH:8][C:3]=1[CH2:4][OH:6]

Participants

7

Reactant 4

HCID 79372,6-LutidineHCID 516892Sodium BicarbonateHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Product 1

HCID 89767711HCID 89767711, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of methyl 2-chloro-4-hydroxybenzoate (4.43 g) and 2,6-lutidine (6.64 mL) in DCM (50 mL) cooled with an ice bath was added triisopropylsilyl trifluoromethanesulfonate (7.66 mL). After being stirred at 0° C. for 1 h, saturated aqueous NaHCO3 was added thereto. The mixture was diluted with Et2O and layers were separated. The aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane). The product was dissolved in diethyl ether (175 mL). To the solution cooled with an ice bath was added lithium aluminum hydride (1.08 g). After being stirred at 0° C. for 30 min, sodium sulfate decahydrate was added thereto. The mixture was filtered through a pad of celite. The filtrate was concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (6.87 g).

Workup

  1. temperaturecooled with an ice bath
  2. customwere separated
  3. extractionThe aqueous layer was extracted with Et2O
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
  8. dissolutionThe product was dissolved in diethyl ether (175 mL)
  9. temperatureTo the solution cooled with an ice bath
  10. additionwas added lithium aluminum hydride (1.08 g)
  11. stirringAfter being stirred at 0° C. for 30 min
  12. additionsodium sulfate decahydrate was added
  13. filtrationThe mixture was filtered through a pad of celite
  14. concentrationThe filtrate was concentrated
  15. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-497df8df20df45dcae921ffc09ab522b
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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