Ethyl propiolate → ethyl 4H,6H,7H-pyrazolo(3,2-c)(1,4)oxazine-2-carboxylate

HRID 1158919노트

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HRID 1158919 반응식
[N:1]1O[C:3]([O-])=[C:4]2[N+:9]=1[CH2:8][CH2:7][O:6][CH2:5]2.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[C:12]#C>CC1C=CC=CC=1C>[N:1]1[N:9]2[C:4]([CH2:5][O:6][CH2:7][CH2:8]2)=[CH:3][C:12]=1[C:11]([O:15][CH2:16][CH3:17])=[O:14]

참가 물질

4

반응물 2

HCID 12182Ethyl propiolate2회HCID 118450916,7-dihydro-4H-[1,2,3]oxadiazolo[4,3-c][1,4]oxazin-8-ium-3-olate

생성물 1

HCID 11845785ethyl 4H,6H,7H-pyrazolo(3,2-c)(1,4)oxazine-2-carboxylate수율 87.1%

시약·촉매·용매 1

HCID 7237O-Xylene용매

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온도
140 °C

실험 절차

To a partial solution of 6,7-dihydro-4H-[1,2,3]oxadiazolo[4,3-c][1,4]oxazin-8-ium-3-olate (3.41 g, 24 mmol) in o-xylene (80 ml), was added ethyl propiolate (2.7 ml, 26 mmol). The mixture was stirred at 140° C. for 3 hr. An additional 2.0 ml (19 mmol) of ethyl propiolate was then added and the mixture was stirred at reflux for 18 hr. The final solution was evaporated under vacuum, and the residue was dissolved in a mixture of methylene chloride and hexanes (1:5). The solution was passed through a pad of silica gel and the filter pad was eluted with methylene chloride-hexanes, followed by ethyl acetate. The ethyl acetate eluent was evaporated and the residue washed with hexanes to give 4.10 g of a white solid; mp 63° C.; MS (ESI) m/z 197.1 (M+H).

후처리

  1. stirringthe mixture was stirred
  2. temperatureat reflux for 18 hr
  3. customThe final solution was evaporated under vacuum
  4. dissolutionthe residue was dissolved in a mixture of methylene chloride and hexanes (1:5)
  5. washthe filter pad was eluted with methylene chloride-hexanes
  6. customThe ethyl acetate eluent was evaporated
  7. washthe residue washed with hexanes

출처 및 근거

ORD 기록
ord-c1426aef44894b14a204df26ddd7b2b3
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812014B2

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