Iodoethane → HCID 86660146, compound

HRID 523924Notes

Reaction equation

HRID 523924 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10](=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:24]1[CH:29]=[C:28]([OH:30])[CH:27]=[CH:26][N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:8].I[CH2:33][CH3:34].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH2:7]([O:9][C:10](=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:24]1[CH:29]=[C:28]([O:30][CH2:33][CH3:34])[CH:27]=[CH:26][N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:8]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178471395HCID 178471395, compound

Product 1

HCID 86660146HCID 86660146, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

K2CO3 (21 mg, 0.15 mmol) was added to II (31 mg, 0.10 mmol) in DMF (2 mL) at it under Ar(g). After 15 min iodoethane (9 μL, 0.11 mmol) was added and the reaction was stirred at 70° C. for 26 h. Brine (50 mL) and EtOAc (25 mL) were added, then the phases were separated, and the aqueous phase was extracted with EtOAc (25 mL). The organic phases were combined then dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (60:40) to furnish III as a colourless oil (16 mg, 43%).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (25 mL)
  3. dry with materialThe organic phases were combined then dried over MgSO4
  4. filtrationfiltered
  5. customsubsequently evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washeluting with hexane/EtOAc (60:40)

Sources & evidence

ORD record
ord-f6aead255068466f8ef0b50dd96ca422
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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