Process for preparing alkyl-4-oxotetrahydrofuran-2-carboxylate
The present invention relates to a novel method for preparing alkyl 4-oxotetrahydrofuran-2-carboxylate (I)
1 . A method for preparing a compound of general formula (I)
in which
R 1 is (C 1 -C 4 ) alkyl,
the method comprising:
reacting a compound of general formula (II)
in which
R 2 is (C 1 -C 4 ) alkyl,
with a compound of general formula (III)
in which R 1 is as defined above,
in the presence of MO—Z in an alcohol Z—OH,
in which
M is an alkali metal ion and
Z is (C 1 -C 4 ) alkyl, not including t-butyl;
forming, in a cyclization reaction, a cyclization product of general formula (IV)
in which R 1 is as defined for formula (I); and
reacting, under non-hydrolytic conditions, the cyclization products in a dealkoxycarbonylation reaction to form the compound of general formula (I).
2 . The method according to claim 1 , wherein:
R 1 is ethyl or methyl,
R 2 is ethyl or methyl,
M is sodium or potassium, and
Z is ethyl or methyl.
3 . The method according to claim 2 , wherein:
R 1 is methyl,
R 2 is methyl,
M is sodium, and
Z is methyl.
4 . The method according to claim 1 , wherein, in addition to the cyclization product having the general formula (IV), intermediates (V) and (VI) also form
in which R 1 is as defined for formula (I) and R 2 is as defined for formula (II), wherein the intermediates (V) and (VI) react further to form the compound of formula (IV).
5 . The method according to claim 1 , wherein the alcohol Z—OH is removed by distillation during the cyclization reaction.
6 . The method according to claim 1 , wherein the cyclization is carried out at a temperature of from 15 to 70° C.
7 . The method according to claim 6 , wherein the cyclization reaction is carried out at a temperature of from 40 to 60° C.
8 . The method according to claim 1 , wherein the cyclization reaction is conducted in the presence of at least one solvent selected from the group consisting of anisole, THF, toluene, xylene and Me-THF.
9 . The method according to claim 8 , wherein the solvent further comprises Z—OH, where Z is (C 1 -C 4 ) alkyl, not including t-butyl.
10 . The method according to claim 8 , wherein the solvent used for the cyclization reaction is an anhydrous solvent.
11 . The method according to claim 1 , characterized in that further comprising metering in the MO—Z in Z—OH.
12 . The method according to claim 1 , further comprising adding NaOMethyl to the cyclization reaction.
13 . The method according to claim 1 , further comprising adding a reagent/solvent to the dealkoxycarbonylation reaction, wherein the reagent/solvent is acetic acid or consists of a mixture of acetic acid and trifluoroacetic acid.
14 . The method according to claim 4 , wherein:
R 1 is ethyl or methyl,
R 2 is ethyl or methyl,
M is sodium or potassium, and
Z is ethyl or methyl.
15 . The method according to claim 14 , wherein:
R 1 is methyl,
R 2 is methyl,
M is sodium, and
Z is methyl.
16 . The method according to claim 5 , wherein:
R 1 is ethyl or methyl,
R 2 is ethyl or methyl,
M is sodium or potassium, and
Z is ethyl or methyl.
17 . The method according to claim 16 , wherein:
R 1 is methyl,
R 2 is methyl,
M is sodium, and
Z is methyl.
18 . The method according to claim 7 , wherein:
R 1 is ethyl or methyl,
R 2 is ethyl or methyl,
M is sodium or potassium, and
Z is ethyl or methyl.
19 . The method according to claim 18 , wherein:
R 1 is methyl,
R 2 is methyl,
M is sodium, and
Z is methyl.
20 . The method according to claim 9 , wherein:
R 1 is methyl,
R 2 is methyl,
M is sodium, and
Z is methyl.