Iodoethane → tert-butyl N-ethyl-N-(prop-2-yn-1-yl)carbamate

HRID 2390666Notes

Reaction equation

HRID 2390666 reaction equation
[H-].[Na+].[CH2:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:4]#[CH:5].[CH2:14](I)[CH3:15]>CN(C=O)C.O>[CH2:14]([N:6]([CH2:3][C:4]#[CH:5])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH3:15]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Product 1

HCID 18366151tert-butyl N-ethyl-N-(prop-2-yn-1-yl)carbamateYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A suspension of sodium hydride (354 mg, 14.2 mmol) in DMF (33 mL) at room temperature was treated with a solution of Example 516A (2.0 g, 12.9 mmol) in DMF (10 mL) and stirred for one hour at room temperature. The solution was cooled to 0° C., treated with ethyl iodide (1.24 mL, 15.5 mmol), stirred for one hour at 0° and overnight at room temperature. The solution was diluted with water (25 mL), extracted with diethyl ether (2×50 mL) and the combined organic layers were washed with brine (30 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel using 5-10% ethyl acetate/hexanes to give the 1.1 g (47% yield) of the desired product. MS (ESI(+)) m/e 184 (M+H)+.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringstirred for one hour at 0° and overnight at room temperature
  3. extractionextracted with diethyl ether (2×50 mL)
  4. washthe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel using 5-10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8d4551e798cc4a009dee989925edb888
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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