Potassium Hydroxide → 5-Nitro-6-(2thiazolylthio)-1-indanone ethylene acetal

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Reaction Conditions

Reaction Steps

The bromide from Step 6 (410 mg, 1.37 mmol) and 2-mercaptothiazole (200 mg, 1.7 mmol) were mixed together in pyridine (3 mL) at room temperature. Aqueous KOH (8M, 213 μL, 1.7 mmol) was added and the resulting mixture was heated with an oil bath at 80° C. for 3 h, then at 100° C. for 1.5 h and finally 75° C. for 16 h. After cooling to room temperature the mixture was diluted and EtOAc and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (from 5% acetone in 2:1 CH2Cl2 -hexanes to 10% acetone in CH2Cl2) yielded 280 mg of the title compound.

Provenance & Evidence