Trimethyl orthoformate
Encyclopedia
Trimethyl orthoformate is a the simplest orthoester
. It is a reagent
used in organic synthesis
for the introduction of a protecting group
for aldehyde
s. The product of reaction of an aldehyde with trimethyl orthoformate is an acetal
. In general cases, these acetals can be deprotected back to the aldehyde by using hydrochloric acid
.
The industrial synthesis of this chemical is from hydrogen cyanide and methanol.
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and hetercyclic ring systems. It is used in the production of the fungicides, azoxystrobin
and picoxystrobin, as well as for some members of the floxacin
family of antibacterial drugs.
A number of pharmaceutical intermediates are also made from trimethyl orthoformate.
Orthoester
In organic chemistry, an orthoester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC3. The name can also refer to any organic compound that contains this functional group. An example of an orthoester is ethyl orthoacetate, CH3C3,...
. It is a reagent
Reagent
A reagent is a "substance or compound that is added to a system in order to bring about a chemical reaction, or added to see if a reaction occurs." Although the terms reactant and reagent are often used interchangeably, a reactant is less specifically a "substance that is consumed in the course of...
used in organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
for the introduction of a protecting group
Protecting group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction...
for aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
s. The product of reaction of an aldehyde with trimethyl orthoformate is an acetal
Acetal
An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals...
. In general cases, these acetals can be deprotected back to the aldehyde by using hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
.
The industrial synthesis of this chemical is from hydrogen cyanide and methanol.
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and hetercyclic ring systems. It is used in the production of the fungicides, azoxystrobin
Azoxystrobin
Azoxystrobin is a fungicide commonly used in agriculture. The substance is used as an active agent protecting plants and fruit/vegetables from fungal diseases.-Origin:...
and picoxystrobin, as well as for some members of the floxacin
Floxacin
Floxacin can refer to* a trade name of the antibiotic ofloxacin* -floxacin, the common stem of fluoroquinolone antibiotics...
family of antibacterial drugs.
A number of pharmaceutical intermediates are also made from trimethyl orthoformate.