Potassium Carbonate → 5-(2,2,3,3,3-Pentafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]([F:33])([C:29]([F:32])([F:31])[F:30])[CH2:20]OS(C(F)(F)F)(=O)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:20][C:19]([F:33])([F:18])[C:29]([F:32])([F:31])[F:30])=[CH:7][N:6]=1)=[O:4]Participants
4
Procedure
In a manner analogous to that described in example 30a), the alkylation of the 5-hydroxy-pyridine-2-carboxylic acid methyl ester with potassium carbonate and trifluoro-methanesulphonic acid 2,2,3,3,3-pentafluoropropyl ester yielded the 5-(2,2,3,3,3-pentafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester as a light yellow oil. MS (ISP): m/z=285 [M]+. b) In a manner analogous to that described in example 30b), the hydrolysis of the 5-(2,2,3,3,3-pentafluoro-propoxy)-pyridine-2-carboxylic acid methyl ester with lithium hydroxide yielded the 5-(2,2,3,3,3-pentafluoro-propoxy)-pyridine-2-carboxylic acid as a white solid. MS (ISP): m/z=271 [M+H]+.
Sources & evidence
- ORD record
- ord-23d4bf7f196142d5b02f26e67c7f888b
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389513B2
Reaction notes
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