Iodoethane → HCID 57152513, compound

HRID 2268725Notes

Reaction equation

HRID 2268725 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:23](I)[CH3:24].[H-].[Na+].C(OCC)(=O)C>C1COCC1.O>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:23][CH3:24])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 57260263HCID 57260263, compound

Product 1

HCID 57152513HCID 57152513, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Benzyloxycarbonylamino-1-propanol t-butyldimethylsilyl ether (10.1 g) was dissolved in THF (250 ml), and to the resulting solution were added under ice-cooling ethyl iodide (5.1 ml) and a 60% sodium hydride (as a mineral oil dispersion) (2.0 g). The resultant mixture was stirred under ice-cooling for 30 minutes and then at room temperature for 15 hours. Ethyl acetate and water were added to the reaction solution obtained. The organic layer so separated was washed with water and then dried over magnesium sulfate. The solvent was evaporated off from the solution, and the residue was purified by a silica gel chromatography, thus affording the titled compound (8.5 g; 80%).

Workup

  1. additionto the resulting solution were added under ice-
  2. temperaturecooling for 30 minutes
  3. customobtained
  4. customThe organic layer so separated
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated off from the solution
  8. customthe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-d42af921dc664e368a26890c6900a1a4
Source dataset
uspto-grants-2001_12
Patent number
US06329338B1

Reaction notes

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