تفاعل #87886

معادلة التفاعل

water

sodium hydride

tetrahydrofuran

2,3-methylenedioxybenzaldehyde

tetrahydrofuran

→

ethyl 2,3-methylenedioxycinnamate

المردود 92.0%

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred for 2 hours during which time it
2. 2
   درجة الحرارةto warm to room temperature
3. 3
   استخلاصextracted with ethyl acetate (3×250 mL)
4. 4
   غسيلThe combined organic extracts were then washed with brine
5. 5
   تجفيفdried (MgSO4)
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe crude product was chromatographed over silica gel
8. 8
   غسيلElution with ethyl acetate/hexanes (1:10)

الإجراء التجريبي

Triethyl phosphonoacetate (4.05 mL, 20.2 mmol) was added dropwise to a stirred suspension of sodium hydride (0.80 g, 20 mmol) in anhydrous tetrahydrofuran (20 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 20 minutes. A solution of 2,3-methylenedioxybenzaldehyde (2.50 g, 16 mmol) in tetrahydrofuran (10 mL) was added dropwise at 0° C. The mixture was stirred for 2 hours during which time it was allowed to warm to room temperature. The mixture was poured into water (250 mL), and extracted with ethyl acetate (3×250 mL). The combined organic extracts were then washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was chromatographed over silica gel. Elution with ethyl acetate/hexanes (1:10) gave ethyl 2,3-methylenedioxycinnamate as a colourless solid (3.50 g, 92%).

المصدر