تفاعل #1004580

معادلة التفاعل

tetrahydrofuran

3-oxobutylbenzoate

tetrahydrofuran

dibromodifluoromethane

tris (dimethylamino)phosphine

→

4,4-difluoro-3-methyl-3-butenyl benzoate

المردود 72.5%

المذيبات

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرىReaction
2. 2
   workup.ADDITIONAfter the end of the drop-wise addition
3. 3
   أخرىthe reaction liquid
4. 4
   أخرىat −20° C
5. 5
   workup.ADDITIONAfter the end of the drop-wise addition
6. 6
   أخرىthe reaction liquid
7. 7
   workup.STIRRINGwas stirred at room temperature overnight
8. 8
   غسيلby washing with dilute hydrochloric acid
9. 9
   تجفيفby drying over anhydrous magnesium sulfate
10. 10
    تركيزconcentrating under reduced pressure
11. 11
    أخرىThe residue was purified by silica gel column chromatography (diisopropyl ether:hexane=1:8)

الإجراء التجريبي

Reaction was carried out under nitrogen atmosphere. To 400 ml of tetrahydrofuran, 46.2 g (0.22 mol) of dibromodifluoromethane was dissolved, followed by drop-wise adding 70.2 g (0.43 mol) of tris (dimethylamino)phosphine at −10° C. After the end of the drop-wise addition, the reaction liquid was stirred at room temperature for 1 hour, and 150 ml tetrahydrofuran solution dissolving with 19.2 g (0.10 mol) of 3-oxobutylbenzoate was further added drop-wise at −20° C. After the end of the drop-wise addition, the reaction liquid was stirred at room temperature overnight. To this mixture, diethyl ether was added, followed by washing with dilute hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate, and concentrating under reduced pressure. The residue was purified by silica gel column chromatography (diisopropyl ether:hexane=1:8) to obtain 16.4 g (yield: 72%) of 4,4-difluoro-3-methyl-3-butenyl benzoate.

المصدر