Process for production of 5-alkoxy-4-hydroxymethylpyrazole compound
The present invention relates to a process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound represented by the general formula (3) which comprises reacting a pyrazole compound represented by the general formula (1) (wherein R 1 is a substituent such as alkyl group, substituted or unsubstituted group or the like, and R 2 is an electron withdrawing group) with a compound represented by the general formula (2) L-R 3 (2) (wherein L is a leaving group and R 3 is a substituent such as substituted or unsubstituted alkyl group or the like) in the presence of a base and formaldehyde.
1. A 5-alkoxy-4-hydroxymethylpyrazole compound represented by formula (4):
wherein R 4 is a C1 to C6 alkyl group, an aryl group which may have a substituent or a hetero-aryl group which may have a substituent, R 5 is a C1 to C6 haloalkyl group, a cyano group or a (C1 to C6 alkoxy)carbonyl group, and R 6 is a C1 to C6 alkyl group which is unsubstituted or substituted with halogen, phenyl group, cyano group or (C1 to C6 alkoxy)carbonyl group, a C3 to C8 cycloalkyl group which is unsubstituted or substituted with halogen, phenyl group, cyano group or (C1 to C6 alkoxy) carbonyl group, a C2 to C6 alkenyl group which is unsubstituted or substituted with halogen, phenyl group, cyano group or (C1 to C6 alkoxy)carbonyl group, or a C2 to C6 alkynyl group which is unsubstituted or substituted with halogen, phenyl group, cyano group or (C1 to C6 alkoxy)carbonyl group.
2. The 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 1 , wherein R 5 is a (mono-, di- or tri-fluoro)methyl group.
3. The 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 1 , wherein R 5 is a trifluoromethyl group.
4. The 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 1 , wherein R 5 is a cyano group.
5. The 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 1 , wherein R 5 is a (C1 to C6 alkoxy)carbonyl group.
6. The 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 1 , wherein R 5 is an ethoxycarbonyl group.
7. The 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 1 , wherein R 4 is a methyl group, R 5 is a trifluoromethyl group, and R 6 is a (mono-, di- or tri-halogen substituted)methyl group.
8. The 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 1 , wherein R 4 is a methyl group, R 5 is a trifluoromethyl group, and R 6 is a difluoromethyl group.
9. A process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound of formula (4) of claim 1 , the process comprising:
reacting a pyrazole compound represented by formula (1):
with a compound represented by formula (2):
L-R 6 (2)
(wherein L is a leaving group and R 4 and R 5 are as defined in claim 1 ) in the presence of a base and formaldehyde.
10. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 9 , wherein the leaving group represented by L is a halogen atom, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, or a benzenesulfonyloxy group which may have a substituent.
11. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 10 , wherein R 5 is a (mono- , di- or tri- fluoro) methyl group.
12. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 10 , wherein R 5 is a trifluoromethyl group.
13. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 10 , wherein R 5 is a cyano group.
14. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 10 , wherein R 5 is a (C1 to C6 alkoxy)carbonyl group.
15. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 10 , wherein withdrawing group represented by R 5 is an ethoxycarbonyl group.
16. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 10 , wherein the leaving group represented by L is a halogen atom.
17. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 10 , wherein the leaving group represented by L is a chlorine atom and R 6 is a difluoromethyl group.
18. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 9 , wherein R 4 is a methyl group, R 5 is a trifluoromethyl group, and the compound represented by formula (2) is a chloro(mono-, di- or tri-halogen substituted) methane.
19. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 9 , wherein R 4 is a methyl group, R 5 is a trifluoromethyl group, and the compound represented by formula (2) is chlorodifluoromethane.
20. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 9 , wherein R 5 is a (mono-, di- or tri-fluoro) methyl group.
21. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 9 , wherein R 5 is a trifluoromethyl group.
22. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 9 wherein R 5 is a cyano group.
23. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 9 , wherein R 5 is a (C1 to C6 alkoxy)carbonyl group.
24. The process for producing a 5-alkoxy-4-hydroxymethylpyrazole compound according to claim 9 , wherein R 5 is an ethoxycarbonyl group.