Tetrahydrofuran → HCID 18771606, compound

HRID 460191Notes

Reaction equation

HRID 460191 reaction equation
[O:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1>CO.O>[O:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 13102629HCID 13102629, compound

Product 1

HCID 18771606HCID 18771606, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 2-phenoxythiazole-4-carboxylate (0.17 g, 0.68 mmol) and LiOH monohydrate (0.14 g, 3.40 mmol) in 2 mL of MeOH, 2 mL of H2O, and 2 mL of THF was stirred at RT overnight, the solvents were removed in vacuo and the residue was diluted with water. The aqueous mixture was acidified with 1N HCl (aq) to pH=1−2, then extracted with EtOAc, the combined organic portions were washed with brine, dried over MgSO4, filtered, removal of the solvents in vacuo yielded the title compound as a white solid. EI-MS =222.4 (M+H)+. Calc'd for C10H7NO3S: 221.01.

Workup

  1. customthe solvents were removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washthe combined organic portions were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customremoval of the solvents in vacuo

Sources & evidence

ORD record
ord-7e3c4d0efc6040bbafde362f58d7d6e6
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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