반응 #41159

반응 방정식

Tetrahydro-4H-pyran-4-one

tert-butyl carbazate

→

N′-(tetrahydro-pyran-4-ylidene)-hydrazinecarboxylic acid tert-butyl ester

수율 62.0%

용매

반응 조건

후처리

1. 1
   기타to precipitate out of solution before the carbazate
2. 2
   workup.ADDITIONDiluted with additional hexanes
3. 3
   온도heated another 15 minutes
4. 4
   온도The mixture was cooled to room temperature
5. 5
   농축concentrated in vacuo
6. 6
   workup.ADDITIONIsopropanol was added to the residue
7. 7
   workup.ADDITIONdiluted with ether
8. 8
   온도chilled
9. 9
   여과The solid was collected by filtration
10. 10
    기타dried in vacuo

실험 절차

Tetrahydro-4H-pyran-4-one (1.002 g, 10.01 mmol, CAS #29943-42-8, purchased from Fluka) was combined with tert-butyl carbazate (1.322 g, 10.00 mmol) in hexanes (10 mL). The mixture was heated in an oil bath at 65-70° C. for 75 minutes. A new precipitate began to precipitate out of solution before the carbazate completely went into solution. The mixture became very thick with the solid precipitate. Diluted with additional hexanes and heated another 15 minutes. The mixture was cooled to room temperature and concentrated in vacuo. Isopropanol was added to the residue and the mixture was stirred vigorously for 5 minutes and then diluted with ether and chilled. The solid was collected by filtration and dried in vacuo to give N′-(tetrahydro-pyran-4-ylidene)-hydrazinecarboxylic acid tert-butyl ester 1.326 g, 62%). A second crop (0.373 g, 17%) was collected from the mother liquor.

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