Allyltributylstannane → n-Trimethylsilylethoxymethyl-5-(3'-allyl-4'-methylphenyl)tetrazole

HRID 2979

Reaction equation

HRID 2979 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:14][Si:15]([CH2:18][CH2:19][O:20][CH2:21]Cl)([CH3:17])[CH3:16].[CH2:23]([Sn](CCCC)(CCCC)CCCC)[CH:24]=[CH2:25]>CN(C=O)C>[CH3:14][Si:15]([CH2:18][CH2:19][O:20][CH2:21][N:13]1[C:9]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH2:25][CH:24]=[CH2:23])[CH:3]=2)=[N:10][N:11]=[N:12]1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 90628AllyltributylstannaneHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 1784182495-(3-Bromo-4-methylphenyl)-2H-tetrazole

Product 1

HCID 69840625n-Trimethylsilylethoxymethyl-5-(3'-allyl-4'-methylphenyl)tetrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 1.0 mmol of this tetrazole, 2.0 mmol of SEMCl in 10 mL DMF was stirred for 1 h. 2.0 mmol of allyltributyltin and 0.1 mmol of Pd(Ph3)4 was added and heated at 70° C. for 14 h. Chromatography provided N-trimethylsilylethoxymethyl-5-(3'-allyl-4'-methylphenyl)tetrazole.

Sources & evidence

ORD record
ord-23c1255e56f24480bb48d53be97ec0f6
Source dataset
uspto-grants-1998_03
Patent number
US05731432

Linked notes

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