반응 #676280

반응 방정식

sodium hypochlorite

prop-2-yn-1-yl benzoate

triethylamine

acetaldoxime

→

desired product

수율 57.1%

(3-Methylisoxazol-5-yl)methyl benzoate

수율 57.1%

용매

chloroform

반응 조건

후처리

1. 1
   기타The layers were separated
2. 2
   추출the aqueous layer was extracted with dichloromethane (2×200 mL)
3. 3
   세척The combined organic layers were washed with water and brine
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타to give the crude product
8. 8
   기타Purification by flash column chromatography (100% hexanes to 30% ethyl acetate/hexanes)

실험 절차

A solution of prop-2-yn-1-yl benzoate (26.0 g, 162 mmol) in chloroform (598 mL) was treated with triethylamine (11.3 mL, 81.2 mmol) and acetaldoxime (14.4 g, 244 mmol). The reaction mixture was cooled to 0° C., treated with sodium hypochlorite (551 mL, 487 mmol) (commercial grade ˜5% aqueous), and stirred overnight at room temperature. The layers were separated and the aqueous layer was extracted with dichloromethane (2×200 mL). The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography (100% hexanes to 30% ethyl acetate/hexanes) gave the desired product (20.1 g, 57%). LCMS calculated for C12H12NO3 (M+H)+: m/z=218.1. found: 218.1.

출처