تفاعل #429282

معادلة التفاعل

(±)-(trans)-N-methoxy-N-methyl-2-(2,3-dihydrobenzofuran-4-yl)cyclopropanecarboxamide

LAH

Potassium hydrogen sulfate

→

oil

المردود 99.0%

(±)-(trans)- 2-(2,3-Dihydrobenzofuran-4-yl)cyclopropanecarboxaldehyde

المردود 99.0%

المذيبات

THF

THF

H2O

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةmaintaining the temperature below -40° C. throughout
2. 2
   أخرىThe cooling bath was removed
3. 3
   أخرىwas immediately recooled to -45° C
4. 4
   درجة الحرارةthe temperature maintained below -30° C. throughout
5. 5
   أخرىThe cooling bath was removed
6. 6
   ترشيحThe mixture was filtered through Celite
7. 7
   غسيلthe filter cake was washed with ether
8. 8
   غسيلThe combined filtrates were then washed with cold 1N HCl, 1N NaOH, and brine
9. 9
   تجفيفThe filtrates were dried over MgSO4
10. 10
    تركيزconcentrated in vacuo

الإجراء التجريبي

A solution of (±)-(trans)-N-methoxy-N-methyl-2-(2,3-dihydrobenzofuran-4-yl)cyclopropanecarboxamide (3.7 g, 15 mmol) in THF (10 mL) was added dropwise to a rapidly stirred suspension of LAH (683 mg, 18 mmol) in THF (50 mL) at -45° C., maintaining the temperature below -40° C. throughout. The cooling bath was removed, the reaction was allowed to warm to 5° C., and then the reaction was immediately recooled to -45° C. Potassium hydrogen sulfate (3.4 g, 25.5 mmol) in H2O (50 mL) was cautiously added dropwise, the temperature maintained below -30° C. throughout. The cooling bath was removed and the suspension was stirred at room temperature for 30 min. The mixture was filtered through Celite and the filter cake was washed with ether. The combined filtrates were then washed with cold 1N HCl, 1N NaOH, and brine. The filtrates were dried over MgSO4, and concentrated in vacuo to give a clear oil (2.6 g, 99%).

المصدر