Ethyl trans-crotonate → Ethyl 3-(ethylsulfanyl)butanoate

HRID 1363012Notes

Reaction equation

HRID 1363012 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH2:9]([S-:11])[CH3:10].[Na+]>CN(C=O)C.O>[CH2:9]([S:11][CH:3]([CH3:4])[CH2:2][C:1]([O:6][CH2:7][CH3:8])=[O:5])[CH3:10]

Participants

5

Reactant 2

HCID 429065Ethyl trans-crotonateHCID 4459711Sodium ethanethiolate

Product 1

HCID 3021670Ethyl 3-(ethylsulfanyl)butanoateYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl crotonate (commercially available, for example, from Aldrich) (2.37 g, 20.8 mmol) was dissolved in DMF (60 ml) and stirred at room temperature. Sodium ethanethiolate (commercially available, for example, from Aldrich) (1.66 g, 19.7 mmol) was added portionwise. On completion of the addition, the mixture was stirred at room temperature overnight. The mixture was diluted with water and extracted with EtOAc (×3). The combined organic solutions were dried (MgSO4), and concentrated in vacuo, for an extensive period of time to remove excess DMF. The residue was applied to a silica cartridge (50 g), eluting with a gradient of EtOAc-cyclohexane (2%-6%) to give the title compound as a colourless oil (527 mg, 14%): 1H NMR δ (CDCl3) 4.16 (2H, q, J=9 Hz), 3.28-3.18 (1H, m), 2.66-2.55 (3H, m), 2.44 (1H, dd, J=15, 8 Hz), 1.33 (3H, d, J=7 Hz), 1.31-1.23 (6H, m).

Workup

  1. additionOn completion of the addition
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with EtOAc (×3)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. concentrationconcentrated in vacuo, for an extensive period of time
  6. customto remove excess DMF
  7. washeluting with a gradient of EtOAc-cyclohexane (2%-6%)

Sources & evidence

ORD record
ord-12321e8369694fb0865fe40f64d150bd
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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