Iodoethane → HCID 23525787, compound

HRID 2415264Notes

Reaction equation

HRID 2415264 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:23])[NH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)([CH3:6])([CH3:5])[CH3:4].I[CH2:25][CH3:26]>O1CCCC1>[C:3]([O:7][C:8](=[O:23])[N:9]([CH2:25][CH3:26])[CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11077303HCID 11077303, compound

Product 1

HCID 23525787HCID 23525787, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (477 mg, 18.88 mmol) (Aldrich, 95%) in tetrahydrofuran (25 mL) was added a solution of [3-(4-nitrophenoxy)propyl]-carbamic acid tert-butyl ester (3.0 g, 10.13 mmol) (from Example 64, Step A) in tetrahydrofuran (15 mL) at 0° C. Upon addition, the mixture was allowed to stir at room temperature for 30 minute, treated with iodoethane (3.76 g, 24.25 mmol) (Aldrich), and heated at 55° C. for one hour before it was quenched with aqueous ammonium chloride (20 mL). The resulting mixture was extracted with ethyl acetate (3×100 mL) and the combined organic extracts were washed with brine and dried (Na2SO4) and evaporated in vacuo. The residue was purified on silica gel with 75:25 hexane/ethyl acetate to give ethyl-[3-(4-nitrophenoxy) propyl]carbamic acid tert-butyl ester (3.15 g, 96%). MS (ES) MH+=325.

Workup

  1. additionUpon addition
  2. temperatureheated at 55° C. for one hour before it
  3. customwas quenched with aqueous ammonium chloride (20 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate (3×100 mL)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was purified on silica gel with 75:25 hexane/ethyl acetate

Sources & evidence

ORD record
ord-4b1228b236294e20956506a71b17de87
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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