Ethyl Acetate → HCID 58545064, compound

HRID 404170Notes

Reaction equation

HRID 404170 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][CH2:34][CH3:35].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][CH2:34][CH3:35])[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 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178471395HCID 178471395, compound

Product 1

HCID 58545064HCID 58545064, compoundYield 80%

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 rt under Ar(g). After 15 min iodopropane (11 μL, 0.11 mmol) was added and the reaction was stirred at 70° C. for 17 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 (28 mg, 80%).

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-1984564cf4a74ed0a127c0ae3d71576b
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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