Ethyl Acrylate → HCID 66924704, compound

HRID 554228Notes

Reaction equation

HRID 554228 reaction equation
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:4][CH2:5][CH2:6][CH3:7])#[C-:2].[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=[CH2:20].CC(C)([O-])C.[K+]>O1CCCC1.O>[CH2:4]([C:3]1[NH:1][CH:2]=[C:19]([C:18]([O:22][CH2:23][CH3:24])=[O:21])[CH:20]=1)[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 23665647Potassium tert-butoxideHCID 457899461-(1-Isocyanopentane-1-sulfonyl)-4-methylbenzene

Product 1

HCID 66924704HCID 66924704, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution (120 mL) of 1-[(1-isocyanopentyl)sulfonyl]-4-methylbenzene (10.8 g) and ethyl acrylate (4.78 mL) in tetrahydrofuran was added dropwise to a solution (80 mL) of potassium tert-butoxide (5.79 g) in tetrahydrofuran while stirring at room temperature over 1 hr. The mixture was further stirred at the same temperature for 30 min, and the reaction product was diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→8:2) to give the title compound as a yellow oil (yield 6.56 g, 78%).

Workup

  1. stirringThe mixture was further stirred at the same temperature for 30 min
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→8:2)

Sources & evidence

ORD record
ord-c35b32b60ffd450fa22a0fecea3f867a
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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