Reacción #62748

Ecuación de reacción

acetic acid

bromocresol green

sodium cyanoborohydride

acetic acid

acetic acid

ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propenoate

→

Ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propanoate

Disolventes

ethanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaHeating
2. 2
   Otrothe ethanol removed under reduced pressure
3. 3
   Extracciónsuccessively extracted with water (125 mL), saturated sodium bicarbonate (3×100 mL) and water (100 mL)
4. 4
   Secadodried over magnesium sulfate
5. 5
   OtroThe volatiles were removed under reduced pressure
6. 6
   Otroto leave an amber oil, 18.22 g (91.4%) which
7. 7
   Otrowas used without further purification

Procedimiento

A mixture of ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propenoate (19.8 g, 0.63 mole) in ethanol (500 mL) under nitrogen was treated with acetic acid (4 mL) and a trace of bromocresol green and heated to reflux. Heating was discontinued and sodium cyanoborohydride (4.4 g, 0.07 mole) in ethanol (100 mL) was co-added with additional acetic acid (11 mL). The mixture was stirred under nitrogen for 2 hr, acetic acid (10 mL) added and the ethanol removed under reduced pressure. The resultant yellow solid was taken up in ethyl acetate (250 mL) and successively extracted with water (125 mL), saturated sodium bicarbonate (3×100 mL) and water (100 mL), then dried over magnesium sulfate. The volatiles were removed under reduced pressure to leave an amber oil, 18.22 g (91.4%) which was used without further purification.

Fuente