反应详情

Reaction was carried out under nitrogen atmosphere. To 650 ml of tetrahydrofuran, 80 g (0.38 mol) of dibromodifluoromethane was dissolved, followed by drop-wisely adding 121 g (0.74 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, followed by further drop-wisely adding 24.9 g (0.17 mol) of methyl 5-oxohexanoate dissolved in 250 ml of tetrahydrofuran, 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 (diethyl ether:hexane=1:4) to obtain 27 g (yield: 88%) of methyl 6,6-difluoro-5-methyl-5-hexenoate.

1. customReaction
2. additionAfter the end of the drop-wise addition
3. customthe reaction liquid
4. additionAfter the end of the drop-wise addition
5. customthe reaction liquid
6. stirringwas stirred at room temperature overnight
7. washby washing with dilute hydrochloric acid
8. dry with materialby drying over anhydrous magnesium sulfate
9. concentrationconcentrating under reduced pressure
10. customThe residue was purified by silica gel column chromatography (diethyl ether:hexane=1:4)