Diethyl Ether → HCID 20674678, compound

HRID 850619Notes

Reaction equation

HRID 850619 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1(O)[CH:9]=[CH:8][CH:7]=[N:6][CH2:5]1.[CH2:12](I)C.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[CH3:26][CH2:27][O:28]CC>>[CH2:1]([O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([O:28][CH2:27][CH3:26])[CH:7]=[N:6][CH:5]=1)[CH3:12]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 67067043HCID 67067043, compound

Product 1

HCID 20674678HCID 20674678, compound

Procedure

A mixture of 3-hydroxy-nicotinic acid methyl ester 15-1 (15 g, 90.8 mmol), ethyl iodide (14.5 ml, 181.6 mmol), cesium carbonate (29.5 g, 90.8 mmol) and DMF (150 mL) was stirred at ambient temperture for 3 hours. The reaction mixture was diluted with Et2O and then washed with 10% K2CO3, brine, dried (MgSO4), and concentrated to give the ester 15-2 as a red oil.

Workup

  1. washwashed with 10% K2CO3, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-42a4cecda27048a2bbb9c250dac5c54b
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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