Lithium Hydroxide → 3-(2-Bromo-thiazol-4-yl)-acrylic acid
Reaction equation
C[O:2][C:3](=[O:12])[CH:4]=[CH:5][C:6]1[N:7]=[C:8]([Br:11])[S:9][CH:10]=1.[OH-].[Li+]>O1CCCC1.O>[Br:11][C:8]1[S:9][CH:10]=[C:6]([CH:5]=[CH:4][C:3]([OH:12])=[O:2])[N:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Dissolve 3-(2-bromo-thiazol-4-yl)-acrylic acid methyl ester (5.9 g, 23.78 mmol) in tetrahydrofuran (48 mL) and add a solution of lithium hydroxide (636 mg, 26.16 mmol) in water (10 mL). Stir the mixture overnight. Extract the mixture with ethyl acetate and wash twice with water. Acidify the aqueous layer with 1N HCl in water until the mixture is at pH 3-4. Filter the resulting white solid, then wash the solid with ethyl acetate, followed by diethyl ether and then water. Dry the white solid to give 5.05 g (91%) of the desired material.
Workup
- extractionExtract the mixture with ethyl acetate
- washwash twice with water
- filtrationFilter the resulting white solid
- washwash the solid with ethyl acetate
- customDry the white solid
Sources & evidence
- ORD record
- ord-0b75bd7791a246c08b3d3c0d8087ad7c
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049013B2
Reaction notes
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