反応 #1771996

反応方程式

dichloroacetic acid

Boc-norvalinol

toluene

EDC

→

Boc-norvalinal

溶媒

dimethylsulfoxide

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   温度to warm to room temperature over a period of 2 h
3. 3
   濃縮The reaction mixture was concentrated
4. 4
   その他to remove the toluene
5. 5
   workup.DISSOLUTIONdissolved in ethyl acetate
6. 6
   洗浄The solution was washed successively with 1N sodium bisulfate, saturated sodium bicarbonate and brine
7. 7
   乾燥dried over sodium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated

実験手順

To Boc-norvalinol (7.77 g, 38 mmol), in anhydrous dimethylsulfoxide (153 mL) and toluene (153 mL) was added EDC (73.32 g, 382 mmol). After the solution was cooled to 0° C., dichloroacetic acid (15.8 mL, 191 mmol) was added dropwise. After addition was complete, the reaction was stirred for 15 min. The solution was allowed to warm to room temperature over a period of 2 h. The reaction mixture was concentrated to remove the toluene, then dissolved in ethyl acetate. The solution was washed successively with 1N sodium bisulfate, saturated sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated to afford crude Boc-norvalinal which was used directly in the next step. TLC Rf=0.84 (40% ethyl acetate/hexanes).

出典