Dibutyltin oxide → HCID 178421826, compound

HRID 1386489Notes

Reaction equation

C([Sn](=O)CCCC)CCC.C[Si]([N:15]=[N+:16]=[N-:17])(C)C.FC(F)(F)C(C1C=CC(C#N)=CC=1)=CC1C=CC2C(C)(C)CCC(C)(C)C=2C=1.[F:46][C:47]([F:74])([F:73])[C:48]([C:65]1[CH:72]=[CH:71][C:68]([C:69]#[N:70])=[CH:67][CH:66]=1)=[CH:49][C:50]1[C:59]([CH3:60])=[CH:58][C:57]2[C:56]([CH3:62])([CH3:61])[CH2:55][CH2:54][C:53]([CH3:64])([CH3:63])[C:52]=2[CH:51]=1>C1(C)C=CC=CC=1>[F:46][C:47]([F:73])([F:74])[C:48]([C:65]1[CH:66]=[CH:67][C:68]([C:69]2[NH:70][N:17]=[N:16][N:15]=2)=[CH:71][CH:72]=1)=[CH:49][CH:50]1[C:59]([CH3:60])=[CH:58][C:57]2[C:56]([CH3:62])([CH3:61])[CH2:55][CH2:54][C:53]([CH3:64])([CH3:63])[C:52]=2[CH2:51]1

Participants

Conditions

Temperature: 110 °C

Procedure

Dibutyl tin oxide (15.1 mg, 10% mol) and trimethylsilyl azide (0.16 ml, 1.22 mmol), are added successively to a solution of the (E) compound 4-[1-trifluoromethyl-2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-1-ethenyl]benzonitrile (0.24 g, 0.60 mmol) in anhydrous toluene (1.25 ml). The reaction medium is heated for 16 hours at reflux (110° C.) under an atmosphere of argon and with magnetic stirring. The mixture is purified by flash chromatography on silica (eluent CH2Cl2 then MeOH:CH2Cl2=5:95) to obtain, after evaporation and washing with pentane and drying, 0.13 g of a white solid, compound (E) 5-[4-[1-trifluoromethyl-2-(5,6,1,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-1-ethenyl]phenyl]-1H-tetrazole (compound CB63237) (yield=49%).

Workup

temperatureThe reaction medium is heated for 16 hours
customThe mixture is purified by flash chromatography on silica (eluent CH2Cl2
customMeOH:CH2Cl2=5:95) to obtain
customafter evaporation
washwashing with pentane
customdrying

Sources & evidence

ORD record: ord-60ba2586da7f4ef4ad54c7913d1d0bc1
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265423B1

Reaction notes

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