Water → HCID 8027287, compound

HRID 1056656Notes

Reaction equation

HRID 1056656 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]N=1.[C:8](OCCBr)(=[O:10])C.O.CN([CH:19]=[O:20])C>>[CH3:8][O:10][C:19](=[O:20])[CH2:4][C@@H:5]1[CH2:6][CH2:7][CH2:2][O:1]1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 135641-Acetoxy-2-bromoethaneHCID 178516071HCID 178516071, compound

Product 1

HCID 8027287HCID 8027287, compound

Conditions

Temperature
70 °C

Procedure

Hydroxy-pyridine 19b (69 g, 0.32 mol) and bromoethyl acetate (64.9 g, 0.39 mol) are dissolved in DMF (500 mL) and heated at 70° C. for 18 h. The solution is cooled to RT, then water is added. The aqueous phase is extracted with EtOAc. The combined organic extracts are washed with H2O, brine, dried (Na2SO4) and concentrated. The residue is purified by chromatography (0 to 10% EtOAc in petroleum ether) to provide ester 19c.

Workup

  1. temperatureThe solution is cooled to RT
  2. extractionThe aqueous phase is extracted with EtOAc
  3. washThe combined organic extracts are washed with H2O, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography (0 to 10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-dec4f4805b614e76bddc7cf6172ef033
Source dataset
uspto-grants-2016_07
Patent number
US09399645B2

Reaction notes

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