تفاعل #1606720

معادلة التفاعل

(methoxymethyl) (triphenyl)phosphonium chloride

n-butyl lithium

6-Fluoro-4-oxo-3,4-dihydro-2H-chromene-7-carbonitrile

→

desired product

(4E)-6-fluoro-4-(methyoxymethylidene)-3,4-dihydro-2H-chromene-7-carbonitrile

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىReaction color
2. 2
   درجة الحرارةThe mixture was cooled to −78° C. and to it
3. 3
   درجة الحرارةThe reaction was let warm to RT
4. 4
   أخرىThe reaction was then quenched with addition of saturated ammonium chloride (5 mL)
5. 5
   استخلاصextracted with dichloromethane
6. 6
   غسيلThe organic phase was washed with brine (5 mL)
7. 7
   تجفيفdried over anhydrous Na2SO4
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىpurified by flash column chromatography (hexane/EtOAc 0-50%)

الإجراء التجريبي

In a 250 ml, round bottom flask, (methoxymethyl) (triphenyl)phosphonium chloride (1.3 g, 3.8 mmol) was dissolved in THF (20 mL). The solution was cooled to −78° C. To above solution was added n-butyl lithium (0.49 mL, 2.50 M in Hexane, 1.05 mmol) dropwise. Reaction color changed to orange. The mixture was cooled to −78° C. and to it was added 6-Fluoro-4-oxo-3,4-dihydro-2H-chromene-7-carbonitrile (100 mg, 0.52 mmol). The reaction was let warm to RT and stirred at RT for 18 hours. The reaction was then quenched with addition of saturated ammonium chloride (5 mL) and extracted with dichloromethane. The organic phase was washed with brine (5 mL), dried over anhydrous Na2SO4, filtered, concentrated and purified by flash column chromatography (hexane/EtOAc 0-50%). The desired product was obtained. LC-MS (IE, m/z): 220.3 [M+1]+.

المصدر