Reaktion #2035319

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature over night
2. 2
   Sonstigebefore being quenched by slow addition of ethanol (10 mL) and water (20 mL) subsequently
3. 3
   FiltrationThe resulting suspension was filtered through celite
4. 4
   Extraktionextracted three times with dichloromethane
5. 5
   EinengenThe combined organic phases were concentrated in vacuo
6. 6
   Sonstigepurified by flash chromatography (SiO2, 0%→30% methanol in dichloromethane)

Vorschrift

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+).

Quelle