반응 #2035319
ord-1df67581b358474cb6983235baa822ec
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반응물
시약
반응 조건
후처리
- 1온도to warm to room temperature over night
- 2기타before being quenched by slow addition of ethanol (10 mL) and water (20 mL) subsequently
- 3여과The resulting suspension was filtered through celite
- 4추출extracted three times with dichloromethane
- 5농축The combined organic phases were concentrated in vacuo
- 6기타purified by flash chromatography (SiO2, 0%→30% methanol in dichloromethane)
실험 절차
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+).