Isopropyl iodide → HCID 58545051, compound

HRID 404172Notes

Reaction equation

HRID 404172 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[CH:33]([CH3:35])[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][CH:33]([CH3:35])[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 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178471395HCID 178471395, compound

Product 1

HCID 58545051HCID 58545051, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

K2CO3 (32 mg, 0.23 mmol) was added to II (53 mg, 0.15 mmol) in DMF (2 mL) at rt under Ar(g). After 15 min 2-iodopropane (16 μL, 0.165 mmol) was added and the reaction was stirred at 70° C. for 3 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 (70:30) to furnish III as a colourless oil (23 mg, 40%).

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 (70:30)

Sources & evidence

ORD record
ord-0785653e5391483484cfd8e2333fd4dc
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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