Reacción #42524

Ecuación de reacción

methyl 5-amino-2-furoate

1-hexen-3-one

benzene

→

methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux for 2 h
2. 2
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
3. 3
   Otroto afford a crude oil
4. 4
   OtroPurification by flash column chromatography (silica, 2:1 hexanes/ethyl acetate)

Procedimiento

A stirred solution of methyl 5-amino-2-furoate (1.4 g, 10 mmol) and 1-hexen-3-one (7 mL, 60 mmol) in benzene (50 mL) was heated to reflux for 2 h. The reaction mixture was concentrated under reduced pressure to afford a crude oil. Purification by flash column chromatography (silica, 2:1 hexanes/ethyl acetate) provided methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate (1.25 g): 1H NMR (300 MHz, CDCl3): δ 6.26-6.23 (m, 1H), 6.09-6.05 (m, 1H), 3.80 (s, 3H), 3.02-2.96 (m, 1H), 2.89-2.84 (m, 1H), 2.42-2.37 (m, 2H), 1.64-1.57 (m, 2H), 0.96-0.88 (m, 3H).

Fuente