反応 #2362432

反応方程式

Mono-tert-butyl malonic acid

magnesium chloride

CDI

2-(4-ethyl-3-iodophenyl)-2-methylpropanoic acid

→

title compound

Tert-butyl 4-(4-ethyl-3-iodophenyl)-4-methyl-3-oxopentanoic acid

溶媒

DME

DME

反応条件

後処理

1. 1
   workup.STIRRINGstirred at room temperature for 1 hr
2. 2
   その他to prepare a solution
3. 3
   workup.ADDITIONThis solution was then added dropwise to the aforementioned mixture
4. 4
   洗浄the resulting solution was washed with DME (90 ml)
5. 5
   workup.STIRRINGstirred at 70° C. for 3 hrs
6. 6
   workup.ADDITIONThe reaction mixture was diluted with isopropyl acetate (225 ml) and heptane (225 ml)
7. 7
   洗浄the organic layer was washed with 2 N hydrochloric acid (684 ml), 0.17 N hydrochloric acid (540 ml), 15% aqueous solution of ammonium chloride (540 ml), 1 N aqueous solution of sodium hydroxide (540 ml) and 15% brine (540 ml) in order
8. 8
   濃縮The organic layer was concentrated under reduced pressure

実験手順

Mono-tert-butyl malonic acid (72.5 g) was dissolved in DME (360 ml), added with TEA (189 ml) and magnesium chloride (29.63 g) and the mixture was stirred for 2 hrs. In a separate vessel, CDI (52.75 g) was added to the DME (360 ml) solution of 2-(4-ethyl-3-iodophenyl)-2-methylpropanoic acid (90 g) and stirred at room temperature for 1 hr to prepare a solution. This solution was then added dropwise to the aforementioned mixture, and the resulting solution was washed with DME (90 ml) and stirred at 70° C. for 3 hrs. The reaction mixture was diluted with isopropyl acetate (225 ml) and heptane (225 ml), and the organic layer was washed with 2 N hydrochloric acid (684 ml), 0.17 N hydrochloric acid (540 ml), 15% aqueous solution of ammonium chloride (540 ml), 1 N aqueous solution of sodium hydroxide (540 ml) and 15% brine (540 ml) in order. The organic layer was concentrated under reduced pressure to obtain the title compound as a crude product, which was used for the next step without further purification.

出典