Ethyl Acetate → HCID 71739072, compound

HRID 449560Notes

Reaction equation

HRID 449560 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:17])[C:13](Br)([CH3:15])[CH3:14])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C(#N)C.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:13]([CH3:15])([CH3:14])[C:12]([O:11][CH2:9][CH3:10])=[O:17])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 71739072HCID 71739072, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-chloropyridin-3-ol (5 g, 38.6 mmol) and ethyl-2-bromo-2-methylpropanoate (6.01 ml, 40.5 mmol) in acetonitrile (50 mL) was added cesium carbonate (27 g, 83 mmol). The material was stirred vigorously for 48 hours. The mixture was taken up in water (100 ml) and ethyl acetate (100 ml) and transferred to a separatory funnel and shaken. The organic phase was collected and the aqueous phase was back extracted with ethyl acetate (2×50 mL). The organic phases were combined, dried (magnesium sulfate), filtered and stripped. The crude material was purified via preparative HPLC (silica gel; 50 g column) eluting with 5-30% ethyl acetate/hexanes to provide the desired product as light white-yellow mobile oil (6.78 g).

Workup

  1. stirringshaken
  2. customThe organic phase was collected
  3. extractionthe aqueous phase was back extracted with ethyl acetate (2×50 mL)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customThe crude material was purified via preparative HPLC (silica gel; 50 g column)
  7. washeluting with 5-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-196e0797932b4f3a8f41ce670bb10d06
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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