Iodoethane → HCID 66989322, compound

HRID 2407773Notes

Reaction equation

HRID 2407773 reaction equation
[CH2:1]([O:3][C:4]1[N:12]=[C:11]([O:13][CH2:14][CH3:15])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](I)[CH3:23]>CN(C)C=O>[CH2:1]([O:3][C:4]1[N:12]=[C:11]([O:13][CH2:14][CH3:15])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:22][CH3:23])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 58503990HCID 58503990, compound

Product 1

HCID 66989322HCID 66989322, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of the compound prepared in Example 294 (1.75 g) and cesium carbonate (2.70 g) in N,N-dimethylformamide (21 mL) was stirred at room temperature for 2 hours. Ethyl iodide (0.663 mL) was added and stirring continued at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue partitioned between a saturated aqueous solution of sodium bicarbonate and ethyl acetate. The combined organic extracts were washed with brine, dried and evaporated in vacuo to a yellow oil and purified by column chromatography on silica gel (10-50% ethyl acetate in hexane) to obtain the title compound (1.6 g) having the following physical data.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 18 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between a saturated aqueous solution of sodium bicarbonate and ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. customevaporated in vacuo to a yellow oil
  8. custompurified by column chromatography on silica gel (10-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-95e80e893be94d8daf9da0ff175e441e
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…