N,N,N',N'-Tetramethylethylenediamine → 2-((Phenylmethoxy)methyl)-5-(tributylstannyl)-2H-tetrazole

HRID 970711Notes

Reaction equation

[CH2:1]([O:8][CH2:9][N:10]1[N:14]=[N:13][CH:12]=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(CCN(C)C)C.[Li]CCCC.[Sn:28](Cl)([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32]>C(OCC)C.O>[CH2:1]([O:8][CH2:9][N:10]1[N:14]=[N:13][C:12]([Sn:28]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:29][CH2:30][CH2:31][CH3:32])=[N:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To. a solution of 2-benzyloxymethyltetrazole (1 mmole) and TMEDA (2 mmole) in 3 mL diethyl ether at −78° C. was added n-BuLi in hexanes (1 mmole). This was let stir for 5 min at −78° C. and then it was added to a precooled (−78° C.) solution of (n-Bu)3SnCl (1 mmole) in 2 mL of diethyl ether. After stirring at −78° C. for 30 min it was diluted with water and diethyl ether. Extraction and chromatography provided 2-benzyloxymethyl-5-(tributylstannyl)tetrazole as a colorless oil.

Workup

stirringAfter stirring at −78° C. for 30 min it
extractionExtraction and chromatography

Sources & evidence

ORD record: ord-fbb5d9795f1f42408441c899923b48fe
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312219B2

Reaction notes

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