反応 #2035319

反応方程式

lithium diisopropylamide

heptane tetrahydrofuran ethylbenzene

1,4-dioxa-spiro[4.5]decane-8-carbonitrile

4-iodotetrahydro-2H-pyran

→

8-(tetrahydropyran-4-yl)-1,4-dioxa-spiro[4.5]decane-8-carbonitrile

8-(Tetrahydropyran-4-yl)-1,4-dioxa-spiro[4.5]decane-8-carbonitrile

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度to warm to room temperature over night
2. 2
   その他before being quenched by slow addition of ethanol (10 mL) and water (20 mL) subsequently
3. 3
   ろ過The resulting suspension was filtered through celite
4. 4
   抽出extracted three times with dichloromethane
5. 5
   濃縮The combined organic phases were concentrated in vacuo
6. 6
   その他purified by flash chromatography (SiO2, 0%→30% methanol in dichloromethane)

実験手順

To a 2M solution of lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene (18 mL, 35.9 mmol, 1.5 eq.) at −78° C. was added dropwise a solution of 1,4-dioxa-spiro[4.5]decane-8-carbonitrile (commercially available or via literature procedure described for example in Becker et al. Synthesis 1992, 11, 1080-1082; 4.0 g, 23.9 mmol) in tetrahydrofuran (40 mL). After stirring for 30 min at −78° C., 4-iodotetrahydro-2H-pyran (5.1 g, 23.9 mmol, 1 eq.) was added carefully. The reaction mixture was allowed to warm to room temperature over night before being quenched by slow addition of ethanol (10 mL) and water (20 mL) subsequently. The resulting suspension was filtered through celite and extracted three times with dichloromethane. The combined organic phases were concentrated in vacuo and purified by flash chromatography (SiO2, 0%→30% methanol in dichloromethane) to give 2.80 g of 8-(tetrahydropyran-4-yl)-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (5). Rt=1.03 min (Method B). Detected mass: 252.3 (M+H+).

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