Réaction #645111

Équation de réaction

N-Benzyl-N-methoxymethyl-N-(trimethylsilyl)methylamine

coumarin

trifluoroacetic acid

→

desired product

Rendement 70.9%

2-benzyl-2,3,3a,9b-tetrahydrochromeno[3,4-c]pyrrol-4(1H)-one

Rendement 70.9%

Solvants

methylene chloride

DCM

Conditions de réaction

Traitement

1. 1
   Lavagewas then washed with NaHCO3 (2 mL) and brine (2 mL) successively
2. 2
   SéchageThe organic phase was dried (over Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   AutreThe residue was purified by CombiFlash (ethyl acetate/hexane 20%)

Mode opératoire

N-Benzyl-N-methoxymethyl-N-(trimethylsilyl)methylamine (1.54 mL, 0.00600 mol) in methylene chloride (0.50 mL) was added to a mixture of coumarin (0.731 g, 0.00500 mol) and of trifluoroacetic acid in DCM (1M, 10 mL) at rt. The resulting mixture was stirred at rt for 1 h and was then washed with NaHCO3 (2 mL) and brine (2 mL) successively. The organic phase was dried (over Na2SO4), filtered, and concentrated. The residue was purified by CombiFlash (ethyl acetate/hexane 20%) to give the desired product (0.99 g).

Source