Potassium Hydroxide → (2-methyl-1,3-thiazol-4-yl)acetic acid

HRID 915677Notes

Reaction equation

HRID 915677 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]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 854815Ethyl (2-methyl-1,3-thiazol-4-yl)acetate

Product 1

HCID 854632(2-methyl-1,3-thiazol-4-yl)acetic acidYield 78.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

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

  1. customthe reaction at room temperature for 1 hour
  2. concentrationConcentrate the solution in vacuo
  3. customto remove the tetrahydrofuran
  4. extractionExtract the aqueous solution with CHCl3
  5. washWash the resulting organic phase with brine (200 mL)
  6. dry with materialdry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9801ff968bbc477b80a857737d104310
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

Loading…