Lithium Hydroxide → HCID 82598401, compound

HRID 2200596Notes

Reaction equation

HRID 2200596 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])=[N:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90403348HCID 90403348, compound

Product 1

HCID 82598401HCID 82598401, compoundYield 99.3%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of ethyl 3-(5-methylthiazol-2-yl)propanoate (0.2 g, 1 mmol) in THF/water (3 mL/3 mL) was added lithium hydroxide (61 mg, 1.5 mmol) portionwise at room temperature. The resulting mixture was stirred for 3 h. The solvent was evaporated and the residue was acidified with conc. HCl to adjust the pH to 1-2. The mixture was partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate and concentrated to afford 3-(5-methylthiazol-2-yl)propanoic acid (0.17 g, 87.7% yield) as a colorless oil. LCMS retention time 0.436 min; LCMS MH+ 172.

Workup

  1. customThe solvent was evaporated
  2. customThe mixture was partitioned between ethyl acetate and water
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f835f4e7aca94475918c9e1ffc00e6a0
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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