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

HRID 1377945노트

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HRID 1377945 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>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([C:13](=[N+:38]=[N-:39])[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

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-diazoacetate수율 91.3%

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-triisopropylbenzenesulfonyl 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 chromatographed on silica (eluent 5% ether/60-80 bp petrol), to afford the the title compound (45.6 g, 91%) as yellow prisms. I.R (film, NaCl) n 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 chromatographed on silica (eluent 5% ether/60-80 bp petrol)

출처 및 근거

ORD 기록
ord-1f4e4bf9492a4d52a778ddc6cd2a2ad6
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665883

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