反応 #72988

反応方程式

1,4-cyclohexanedione mono-ethylene ketal

nitromethane

sodium ethoxide

→

8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-ol

収率 40.0%

溶媒

ethanol

ethanol

反応条件

後処理

1. 1
   濃縮was concentrated under reduced pressure to a brown oil that
2. 2
   その他was partitioned between water (100 mL) and dichloromethane (100 mL)
3. 3
   抽出The aqueous layer was extracted with dichloromethane (3×100 mL)
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated to a light brown oil
7. 7
   その他Purification by flash chromatography (silica gel, 40% ethyl acetate/hexanes)

実験手順

To a solution of 1,4-cyclohexanedione mono-ethylene ketal (30.0 g, 192 mmol) and nitromethane (15.6 mL, 288 mmol) in ethanol (18 mL) was added a solution of sodium ethoxide in ethanol (2.67 M, 3.4 mL, 9.6 mmol). The solution was stirred at room temperature (rt) for 5 days (d), then was concentrated under reduced pressure to a brown oil that was partitioned between water (100 mL) and dichloromethane (100 mL). The aqueous layer was extracted with dichloromethane (3×100 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to a light brown oil. Purification by flash chromatography (silica gel, 40% ethyl acetate/hexanes) provided the product 8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-ol as a clear oil (16.7 g, 40%) that slowly formed clear crystals overnight.

出典