Isopropyl iodide → HCID 58545051, compound

HRID 523928Notes

Reaction equation

HRID 523928 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 it 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-a122ee59b3234d409be29140f4fd7c2e
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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