Potassium Hydroxide → (2-Methyl-1,3-thiazol-4-yl)acetic acid
Reaction equation
C([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([CH3:11])[S:9][CH:10]=1)C.[OH-].[K+]>O1CCCC1.O>[CH3:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:12])=[O:3])[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Prepare a solution of (2-methylthiazol-4-yl)acetic acid ethyl ester (17 g, 92 mmol) in tetrahydrofuran/water (1:1, 400 mL). Add potassium hydroxide (10.3 g, 184 mmol). Stir the reaction at room temperature for 1 hour. Concentrate the solution in vacuo to remove the tetrahydrofuran then acidify with 1N HCl. Extract the aqueous solution with CHCl3. Wash the resulting organic phase with brine (200 mL), dry (Na2SO4), filter and concentrate in vacuo to afford (2-methylthiazol-4-yl)acetic acid (11.3 g) as a solid. 1H NMR (CDCl3) δ 7.00 (s, 1H), 3.85 (s, 2H), 2.71 (s, 3H).
Workup
- customthe reaction at room temperature for 1 hour
- concentrationConcentrate the solution in vacuo
- customto remove the tetrahydrofuran
- extractionExtract the aqueous solution with CHCl3
- washWash the resulting organic phase with brine (200 mL)
- dry with materialdry (Na2SO4)
- filtrationfilter
- concentrationconcentrate in vacuo
Sources & evidence
- ORD record
- ord-9801ff968bbc477b80a857737d104310
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265246B2
Reaction notes
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