Chlorotrimethylsilane → 1-{2-[(Trimethylsilyl)oxy]ethyl}-1H-pyrrole-2,5-dione

HRID 1600520Notes

Reaction equation

HRID 1600520 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH:7]=[CH:6][C:5]1=[O:10].C(N(CC)CC)C.Cl[Si:19]([CH3:22])([CH3:21])[CH3:20]>ClCCl>[CH3:20][Si:19]([CH3:22])([CH3:21])[O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH:7]=[CH:6][C:5]1=[O:10]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 458487N-(2-Hydroxyethyl)maleimide

Product 1

HCID 218298161-{2-[(Trimethylsilyl)oxy]ethyl}-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-hydroxyethyl)maleimide (0.2 g, 1.41 mmol) in dry dichloromethane (10 ml) and triethylamine (0.22 ml, 1.57 mmol) at 0° C. was added chlorotrimethylsilane (TMS-Cl, 0.2 ml, 1.57 mmol). After stirring for 1 hour at room temperature, TLC analysis (ethyl acetate/petroleum ether 1:1) indicated one spot (Rf=0.67). Solvent was removed in vacuo and the residue was dissolved in dichloromethane and filtered through a small silica gel column eluting with dichloromethane. The fractions containing product were pooled and evaporated in vacuo to afford N-(2-trimethylsiloxyethyl)-maleimide (formula II) as colorless flakes (0.3 g; 100% yield).

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. filtrationfiltered through a small silica gel column
  4. washeluting with dichloromethane
  5. additionThe fractions containing product
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e4ebd80f2e964663addf7585968b596d
Source dataset
uspto-grants-1999_11
Patent number
US05976857

Reaction notes

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