1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 2-(3,5-bis(trifluoromethyl)phenyl)-2-diazoacetate

HRID 962476노트

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HRID 962476 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:38]=[N+:39]=[N-])(=O)=O)(C)C.N12CCCN=C1CCCCC2>C(#N)C>[N+:38](=[C:13]([C:5]1[CH:4]=[C:3]([C:2]([F:18])([F:19])[F:1])[CH:8]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:6]=1)[C:14]([O:16][CH3:17])=[O:15])=[N-:39]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 10401718Methyl 2-[3,5-bis(trifluoromethyl)phenyl]acetate

생성물 1

HCID 54200568Methyl 2-(3,5-bis(trifluoromethyl)phenyl)-2-diazoacetate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
-5 °C

실험 절차

To methyl 3,5-bis(trifluoromethyl)phenylacetate (43.5 g, 160 mmol), in dry acetonitrile (250 ml), cooled to -5° C., was added 2,4,6-triisopropyl benzenesulfonyl azide (52.7 g). To the resulting solution was added 1,8-diazabicyclo[5.4.0]undec-7-ene (25.5 ml), and the mixture was stirred at -5° C. for 1 hour. The mixture was warmed to room temperature, and then stirred for 0.5 hour. The solvents were evaporated at reduced pressure and the residue purified by chromatography on silica gel (eluant 5% diethyl ether/petroleum ether), to afford the the title compound as yellow prisms. I.R (film, NaCl) 1740, 2140 cm-1.

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 0.5 hour
  3. customThe solvents were evaporated at reduced pressure
  4. customthe residue purified by chromatography on silica gel (eluant 5% diethyl ether/petroleum ether)

출처 및 근거

ORD 기록
ord-6513d083cec3496bb7e47ec90921d762
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760018

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