反応 #422399

反応方程式

HBr

methyl 4-bromo-2-methoxy-2-methylpent-4-enoate

acetonitrile

N-bromosuccinimide

→

title compound

収率 92.8%

methyl 5-bromo-2-methoxy-2-methyl-4-oxopentanoate

収率 92.8%

溶媒

dichloromethane

water

反応条件

後処理

1. 1
   洗浄washed twice with saturated sodium bicarbonate
2. 2
   その他dried
3. 3
   その他evaporated
4. 4
   その他The residue was purified by chromatography on silica gel
5. 5
   洗浄eluting with 10% ethyl acetate/hexane

実験手順

To a 125 mL round-bottom flask, methyl 4-bromo-2-methoxy-2-methylpent-4-enoate (0.525 g, 2.21 mmol) was added acetonitrile (8 mL), water (2 mL) and N-bromosuccinimide (0.493 g, 2.77 mmol). A catalytic amount of 1M HBr was added (0.066 mL, 0.066 mmol). The resulting solution was agitated overnight, diluted with 50 mL of dichloromethane and washed twice with saturated sodium bicarbonate, dried and evaporated. The residue was purified by chromatography on silica gel, eluting with 10% ethyl acetate/hexane to provide the title compound (0.52 g, 92.8% yield) as clear oil.

出典