2-Methoxyethanol → HCID 15180743, compound

Participants

Reaction Steps

In a 100 cm3 three neck flask fitted with a thermometer, a condenser with a bubbler and an argon inlet, 2.35 g of 3-chloroacetyl-l-tosyl pyrrole 3 (8 mmoles) was introduced together with 50 cm3 of 2-methoxy ethanol. 3 g of lithium bromide was added and the solution was set under reflux and argon flux during 24 hours. After cooling, 20 cm3 of 5 N aqueous solution of sodium hydroxide was added and the mixture was maintained under stirring at ambient temperature during 24 hours. 20 cm3 of brine was added and after decantation, the aqueous layer was extracted with ethyl acetate. The combine organic layer was washed with brine, dried and evaporated. The crude product (1.4 g) was dissolved in a little amount of methanol and separated on a silica gel column (150 g; 60-200 μm; eluting with 1-29-70 acetic acid-ethyl acetate-heptane) to give 0.42 g of purified product 4 (M=183, yield: 29%). NMR: (CDCl3) ppm 7.5 1H; 6.7 1H; 6.6 1H; 4.5 s 2H; 3.6 4H; 3.3 s 3H.

Provenance & Evidence