Réaction #411759

Équation de réaction

3,3-dimethyl-1-(2-pent-4-enoylpyrrolidinyl)pentane-1,2-dione

4-benzyloxybromobenzene

tri(orthotolyl)phosphine

→

3,3-dimethyl-1-(2-{5-[4-(phenylmethoxy)phenyl]pent-4-enoyl}pyrrolidinyl)pentane-1,2-dione

Rendement 60.1%

Solvants

triethylamine

Conditions de réaction

Traitement

1. 1
   ConcentrationThe mixture was concentrated in vacuo
2. 2
   Autrepurified on a silica gel column
3. 3
   Lavageeluting with a gradient from 10% ethyl acetate/hexane to 20% ethyl acetate/hexane

Mode opératoire

A solution of 3,3-dimethyl-1-(2-pent-4-enoylpyrrolidinyl)pentane-1,2-dione (1.73 g; 6.20 mmol), 4-benzyloxybromobenzene (1.80 g; 6.83 mmol), palladium (II) acetate (70 mg; 0.31 mmol), and tri(orthotolyl)phosphine (380 mg; 1.24 mmol) in triethylamine (23 ml) was refluxed overnight. The mixture was concentrated in vacuo and purified on a silica gel column, eluting with a gradient from 10% ethyl acetate/hexane to 20% ethyl acetate/hexane, to obtain 1.72 g (60%) of 3,3-dimethyl-1-(2-{5-[4-(phenylmethoxy)phenyl]pent-4-enoyl}pyrrolidinyl)pentane-1,2-dione as a yellow oil.

Source