Iodoethane → Ethyl 2-(methylsulfonyl)butanoate

HRID 84281

Reaction equation

HRID 84281 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[CH3:2].[H-].[Na+].I[CH2:14][CH3:15].[Cl-].[NH4+]>CN(C=O)C.O>[CH3:9][S:6]([CH:5]([CH2:14][CH3:15])[C:4]([O:3][CH2:1][CH3:2])=[O:10])(=[O:8])=[O:7]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 78201Ethyl methanesulfonylacetate

Product 1

HCID 10702984Ethyl 2-(methylsulfonyl)butanoateYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl(methylsulfonyl)acetate (0.79 mL, 5.8 mmol, 1.0 equiv) was added dropwise via syringe to a mixture of sodium hydride (0.25 g 60% in mineral oil, 6.1 mmol, 1.1 equiv) in DMF (20 mL) at room temperature. The mixture was allowed to stir for 30 min, after which time 1-iodoethane (0.48 mL, 5.8 mmol, 1.0 equiv) was added. The reaction was allowed to stir overnight. A solution of saturated ammonium chloride (10 mL) and water (10 mL) were added, and the resulting mixture was extracted with diethyl ether (1×25 mL). The organic phase was separated, washed with water (1×10 mL), brine (1×5 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude material was purified by flash chromatography (2:1-0:1 heptane/ethyl acetate) to provide a white solid (0.29 g, 26%). MS (LCMS) m/z 195.4 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.05 (t, J=7.41 Hz, 3 H) 1.33 (t, J=7.12 Hz, 3 H) 1.99-2.25 (m, 2 H) 2.99 (s, 3 H) 3.66 (dd, J=10.54, 3.90 Hz, 1 H) 4.30 (q, J=7.22 Hz, 2 H).

Workup

  1. stirringto stir overnight
  2. extractionthe resulting mixture was extracted with diethyl ether (1×25 mL)
  3. customThe organic phase was separated
  4. washwashed with water (1×10 mL), brine (1×5 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography (2:1-0:1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5ce3a8b3c4d3486284baee79c497dd0d
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Linked notes

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