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Cas Database

783321-42-6

783321-42-6

Identification

  • Product Name:C13H22N2Si

  • CAS Number: 783321-42-6

  • EINECS:

  • Molecular Weight:234.417

  • Molecular Formula: C13H22N2Si

  • HS Code:

  • Mol File:783321-42-6.mol

Synonyms:C13H22N2Si

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Relevant articles and documentsAll total 1 Articles be found

A general procedure for the esterification of carboxylic acids with diazoalkanes generated in situ by the oxidation of N-tert- butyldimethylsilylhydrazones with (difluoroiodo)benzene

Furrow, Michael E.,Myers, Andrew G.

, p. 12222 - 12223 (2004)

The bimolecular reaction of carboxylic acids with diazoalkanes to form esters is among the mildest and most efficient of organic transformations but is seldom used in synthesis beyond the important case of methyl esterification. This is largely a consequence of the inaccessibility and poor stability of higher diazoalkanes as substrates. In this work we describe a new method for the synthesis of diazoalkanes by the oxidation of N-tert-butyldimethylsilylhydrazones (TBSHs) with (difluoroiodo)benzene, a reagent heretofore unexplored in the context of hydrazone oxidation. When conducted in the presence of a carboxylic acid substrate, the oxidation leads to efficient esterification in situ. In addition to greatly extending the range of diazoalkanes that are now available for esterifications, this new protocol offers significant advantages with regard to safety, for diazo intermediates are neither isolated nor achieve appreciable concentrations during the reaction. Copyright

Process route upstream and downstream products

Process route

1,2-bis(tert-butyldimethylsilyl)hydrazine
10000-20-1

1,2-bis(tert-butyldimethylsilyl)hydrazine

benzaldehyde
100-52-7

benzaldehyde

C<sub>13</sub>H<sub>22</sub>N<sub>2</sub>Si
783321-42-6

C13H22N2Si

Conditions
Conditions Yield
With scandium tris(trifluoromethanesulfonate); In dichloromethane; acetonitrile; at 0 - 23 ℃; for 2.75h;
100%
1,2-bis(tert-butyldimethylsilyl)hydrazine
10000-20-1

1,2-bis(tert-butyldimethylsilyl)hydrazine

benzaldehyde
100-52-7

benzaldehyde

C<sub>13</sub>H<sub>22</sub>N<sub>2</sub>Si
783321-42-6

C13H22N2Si

Conditions
Conditions Yield
With scandium tris(trifluoromethanesulfonate); In dichloromethane; acetonitrile; at 0 - 23 ℃; for 2.75h;
100%

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