Dibutyltin oxide → HCID 178438909, compound

HRID 1386487Notes

Reaction equation

C([Sn](=O)CCCC)CCC.C[Si]([N:15]=[N+:16]=[N-:17])(C)C.C[C:19]1[C:20]([CH:33]([C:36]2[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][CH:37]=2)[CH:34]=[CH2:35])=[CH:21][C:22]2[C:23]([CH3:32])([CH3:31])[CH2:24][CH2:25][C:26]([CH3:30])([CH3:29])[C:27]=2[CH:28]=1.CC1(C)CCC(C)(C)C2C=C(C(C3C=CC(C#N)=CC=3)C=C)C=CC1=2>C1(C)C=CC=CC=1>[CH3:29][C:26]1([CH3:30])[CH2:25][CH2:24][C:23]([CH3:31])([CH3:32])[C:22]2[CH:21]=[C:20]([CH:33]([C:36]3[CH:43]=[CH:42][C:39]([C:40]4[NH:41][N:17]=[N:16][N:15]=4)=[CH:38][CH:37]=3)[CH:34]=[CH2:35])[CH:19]=[CH:28][C:27]1=2

Participants

Conditions

Temperature: 110 °C

Procedure

Dibutyl tin oxide (75 mg, 10% mol) and trimethylsilyl azide (0.97 ml, 7.28 mmol), are added successively to a solution of the (Z) compound 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]benzonitrile (1.20 g, 3.64 mmol) in anhydrous toluene (6.25 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, washing with hexane and drying at the palette pump, 0.99 g of a white powder, the compound (Z) 5-[4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]phenyl]-1H-tetrazole (compound CB92834) (yield=73%).

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 hexane
dry with materialdrying at the palette pump, 0.99 g of a white powder

Sources & evidence

ORD record: ord-4ad096f769dd4e648172e9c4e6674873
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265423B1

Reaction notes

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