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

HRID 962476Notes

Reaction equation

[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]

Participants

Conditions

Temperature: -5 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-6513d083cec3496bb7e47ec90921d762
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05760018

Reaction notes

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