Water → HCID 20097963, compound

HRID 1768881Notes

Reaction equation

HRID 1768881 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].O>CN(C)C=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 10796Cesium carbonateHCID 110639836-iodopyridin-3-ol

Product 1

HCID 20097963HCID 20097963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of one gram of 2-iodo-5-hydroxypyridine (prepared as by Edgar, K. J. & Falling, S. N.; (1990) J. Org. Chem., 55: 5287) in dimethylformamide (14 ml) was added cesium carbonate (1.55 g) and bromooctane (1.56 ml). The reaction was allowed to stir for 100 hrs, at which time it was poured into water and extracted with 1:1 hexane:ethyl acetate. The combined organics were washed with brine and dried over sodium sulfate and potassium carbonate. The solvent was removed in vacuo to give a yellow oil. This oil was purified by flash chromatography using 10% ethyl acetate in hexanes as the eluent, giving a clear oil as a product.

Workup

  1. extractionextracted with 1:1 hexane
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate and potassium carbonate
  4. customThe solvent was removed in vacuo
  5. customto give a yellow oil
  6. customThis oil was purified by flash chromatography
  7. customgiving a clear oil as a product

Sources & evidence

ORD record
ord-09ca24a724154da08278c17b40abc599
Source dataset
uspto-grants-1995_01
Patent number
US05380460

Reaction notes

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