反応 #362581

反応方程式

Mercaptoacetic acid

sodium methoxide

cyclopentene oxide

→

trans-[(2-Hydroxycyclopentyl)thio]acetic acid

溶媒

methanol

反応条件

後処理

1. 1
   その他The ice bath was removed
2. 2
   温度the reaction was refluxed for 45 minutes
3. 3
   workup.ADDITIONmade acidic by the addition of 4N hydrochloric acid
4. 4
   workup.ADDITIONWater (100 ml) was added
5. 5
   抽出the mixture was extracted twice with 150 ml of diethyl ether
6. 6
   洗浄The combined diethyl ether extracts were washed with water (50 ml)
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated to an oil with a rotary evaporator

実験手順

Mercaptoacetic acid (22.5 g 0.244 mole) was added to a cold (+5° C.) solution of sodium methoxide [prepared from sodium (11.2 g, 0.488 mole)] in methanol (125 ml). After stirring for 20 minutes, cyclopentene oxide (19.5 g, 0.23 mole) was added dropwise over 20 minutes to the cold solution. The ice bath was removed and the reaction was refluxed for 45 minutes. The reaction was cooled to room temperature and made acidic by the addition of 4N hydrochloric acid. Water (100 ml) was added and the mixture was extracted twice with 150 ml of diethyl ether. The combined diethyl ether extracts were washed with water (50 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to an oil with a rotary evaporator. The structure was confirmed by NMR spectroscopy.

出典