Cesium carbonate → HCID 21699787, compound

HRID 618160Notes

Reaction equation

HRID 618160 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][O:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH3:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrateHCID 178418642HCID 178418642, compound

Product 1

HCID 21699787HCID 21699787, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxypyridine (10 g, 105 mmol), ethyl 4-bromobutyrate 12-1 (15.0 ml, 105 mmol) and Cs2CO3 (34.2 g, 105 mmol) in DMF (100 ml) was stirred at room temperature for 24 h. The reaction was filtered and the filtrate diluted with ethyl acetate (300 ml) and washed with water (4×100 ml) and brine (100 ml) then dried (Na2SO4), filtered, and evaporated. The resulting oil was purified by chromatography on silica gel (3% CH3OH/CH2Cl2) to give 12-2 as a colorless glass.

Workup

  1. filtrationThe reaction was filtered
  2. additionthe filtrate diluted with ethyl acetate (300 ml)
  3. washwashed with water (4×100 ml) and brine (100 ml)
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting oil was purified by chromatography on silica gel (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-56d1d016a33a4ae9b7f765e0436c3187
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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