Sulfuric Acid → ethyl 3,3-bis(4-fluorophenyl)-2-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]-2-propenoate

HRID 974459Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:9]([C:15]2[NH:19][N:18]=[N:17][N:16]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH3:27][C:28](=[CH2:30])[CH3:29].OS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[C:9]([C:15]2[N:16]=[N:17][N:18]([C:28]([CH3:30])([CH3:29])[CH3:27])[N:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -50 °C

Procedure

To a stirred suspension of 10 g of ethyl 3,3-bis(4-fluorophenyl)-2-(1H-tetrazol-5-yl)-2-propenoate in 250 mL dry diethyl ether cooled at -50° C. was slowly added 60 mL of liquid isobutylene (previously condensed from gaseous material in a dry ice-alcohol bath). With continued stirring and cooling, 50 mL of concentrated H2SO4 was added slowly and carefully. The mixture was then sealed in a stainless steel Parr container and stirred at -30° C. for 40 hours. After releasing the pressure, the mixture was added slowly and carefully to excess saturated NaHCO3 solution. The aqueous mixture was extracted with diethyl ether, dried over Na2SO4 and concentrated in vacuo to give 7.8 g (67.8%) of the title compound, m.p. 143°-144° C.

Workup

custompreviously condensed from gaseous material in a dry ice-alcohol bath)
temperaturecooling
stirringstirred at -30° C. for 40 hours
extractionThe aqueous mixture was extracted with diethyl ether
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-67788b5eb50d46e1a2682c57ebc000df
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05068346

Reaction notes

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