Ethyl 2-vinylthiazole-5-carboxylate → Ethyl 2-ethylthiazole-5-carboxylate

HRID 70903Notes

Reaction equation

HRID 70903 reaction equation
[CH:1]([C:3]1[S:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:7]=1)=[CH2:2].[H][H]>CO.[Pd]>[CH2:1]([C:3]1[S:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 59607571Ethyl 2-vinylthiazole-5-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57438029Ethyl 2-ethylthiazole-5-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-vinylthiazole-5-carboxylate (400 mg, 2.18 mmol) in MeOH (7 mL) is added 10% wt. Pd/C (267 mg, 0.25 mmol) at room temperature. After stirring at room temperature under a balloon of hydrogen for 1 hour, the crude is filtered to remove Pd/C. The filtrate is concentrated to give ethyl 2-ethylthiazole-5-carboxylate (404 mg). HPLC retention time=0.60 minutes (condition B); MS (m+1)=186.3; 1H NMR (400 MHz, CD3OD) δ ppm 1.35 (t, J=7.3 Hz, 2 H) 1.39 (t, J=7.20 Hz, 2 H) 3.07 (q, J=7.58 Hz, 2 H) 4.35 (q, J=7.16 Hz, 2 H) 8.22 (s, 1 H)

Workup

  1. filtrationthe crude is filtered
  2. customto remove Pd/C
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-05d9a0fbe19f455f9a9c5bb972f06a90
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

Loading…