Water → Ethyl 3-(5-methylthiazol-2-yl)benzoate

HRID 594231Notes

Reaction equation

HRID 594231 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:13][C:14]1[S:18][C:17]([Sn](CCCC)(CCCC)CCCC)=[N:16][CH:15]=1.O.CCOC(C)=O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:13][C:14]1[S:18][C:17]([C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 143542Ethyl 3-iodobenzoateHCID 164271315-Methyl-2-(tributylstannyl)thiazole

Product 1

HCID 69085699Ethyl 3-(5-methylthiazol-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of commercially available ethyl 3-iodobenzoate (485 mg; 1.75 mmol), 5-methyl-2-(tributylstannyl)thiazole (685 mg; 1.76 mmol), and PdCl2(PPh3)2 (123 mg; 0.17 mmol) in anh. THF (10 ml) was heated to 75° C., under nitrogen, for 18 h. In order to complete this reaction, the resulting reaction mixture was then heated to 85° C. for 8 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=1/1) afforded ethyl 3-(5-methylthiazol-2-yl)benzoate as an orange oil. LC-MS (conditions A): tR=0.88 min.; [M+H]+: 247.98 g/mol.

Workup

  1. customthis reaction
  2. customthe resulting reaction mixture
  3. temperaturewas then heated to 85° C. for 8 h
  4. temperatureAfter cooling to rt
  5. extractionThe separated aq. layer was further extracted with AcOEt
  6. washThe mixed organic layers were washed with brine
  7. dry with materialdried over anh. MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customPurification by FC (heptane/AcOEt=1/1)

Sources & evidence

ORD record
ord-6137e820a70e4b369a7310a0695ce480
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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