반응 #1781704

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

methyl iodide

ammonium chloride

→

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

수율 101.4%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred 30 min at 0° C.
2. 2
   기타30 min
3. 3
   기타at room temperature
4. 4
   추출It was extracted with ether (3×150 mL)
5. 5
   건조dried over anhydrous Na2SO4
6. 6
   농축concentrated
7. 7
   기타Drying under vacuum for 30 min

실험 절차

A 1.6M solution of Butyllithium in THF (14.6 mL, 23.3 mmol) was slowly added over 10 min to a solution of diisopropylamine (3.54 mL, 25.15 mmol) in 11 mL of anhydrous THF at −40° C. under nitrogen. The resulting mixture was stirred for 30 min at −40° C. and the solution of lithium diisopropylamide obtained was transferred dropwise over 15 min to a 0° C. solution of 1,4-Dioxa-spiro[4.5]decane-8-carbonitrile (3.00 g, 17.9 mmol) in 25 of anhydrous THF. The reaction mixture was stirred 15 min at 0° C. and methyl iodide (3.35 mL, 53.8 mmol) was added dropwise over 15 min. The resulting mixture was stirred 30 min at 0° C. then, 30 min at room temperature. A portion of 20 mL of saturated aqueous ammonium chloride was added. It was extracted with ether (3×150 mL). The organic portions were combined, dried over anhydrous Na2SO4 and concentrated. Drying under vacuum for 30 min afforded the desired 8-methyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile as a yellow solid (3.29 g, 101%).

출처