Tetrahydrofuran → HCID 68998953, compound

HRID 230786Notes

Reaction equation

HRID 230786 reaction equation
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)(OCC)=O)C.CC(C)([O-])C.[K+].C1COCC1.[CH:30]([C:32]1[S:33][CH:34]=[CH:35][N:36]=1)=O>O>[S:33]1[CH:34]=[CH:35][N:36]=[C:32]1/[CH:30]=[CH:9]/[C:10]1[CH:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 27349031,3-Thiazole-2-carbaldehydeHCID 137458014-[(Diethoxyphosphoryl)methyl]benzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 68998953HCID 68998953, compoundYield 1.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(diethoxyphosphorylmethyl)benzenecarboxylic acid (440 mg) produced according to JP-A 11-60537, potassium tert-butoxide (340 mg) and THF (5.5 mL) was stirred at room temperature for about 1.5 hours, and then a THF solution (1.0 mL) of 2-formylthiazole (200 mg) was dropwise added thereto. After heated overnight under reflux, water was added to the reaction solution, and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/methanol=9/1), and the resulting purified product was further purified through reversed-phase HPLC to obtain the entitled compound (7 mg).

Workup

  1. customproduced
  2. temperatureAfter heated overnight
  3. temperatureunder reflux
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated off under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/methanol=9/1)
  8. customthe resulting purified product
  9. customwas further purified through reversed-phase HPLC

Sources & evidence

ORD record
ord-7d7945097bf14eb2bdbe16916d7bc4c4
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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