Propargyl alcohol → Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

HRID 58522

반응식

HRID 58522 반응식
[CH2:1]([OH:4])[C:2]#[CH:3].[N+:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])([O-])=[O:6].C1N2CCN(CC2)C1>C(O)C>[OH:4][CH2:1][C:2]1[O:6][N:5]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:3]=1

참가 물질

5

반응물 3

HCID 7859Propargyl alcoholHCID 9237DabcoHCID 69379Ethyl nitroacetate

생성물 1

HCID 8027233Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate수율 81%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

To a mixture of propargyl alcohol (1.0 mL; 16.76 mmol) and ethyl 2-nitroacetate (3.79 mL; 33.52 mmol) in ethanol (23.5 mL) in an Ace pressure tube was added 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.194 g; 1.68 mmol). The tube was heated at 80° C. for 72 h. After cooling, the mixture was evaporated to dryness and the residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane) to yield 2.32 g (81%) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil.

후처리

  1. temperatureAfter cooling
  2. customthe mixture was evaporated to dryness
  3. customthe residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-2f958587927640de86d953d3ffdfc723
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

연결된 노트

불러오는 중…