Ammonium Chloride → Methyl[4-hydroxy-4-(1-methylpiperidin-4-yl)-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl]acetate

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Reaction Steps

A Grignard reagent prepared from magnesium (2.8 g, 116 mmol), 4-chloro-1-methylpiperidine (15.5 mL, 116 mmol), and THF (180 mL) was ice-cooled, and a THF (120 mL) solution of the compound obtained in Example 22 (18.5 g, 58 mmol) was added dropwise thereto. After allowing the mixture to react for 30 minutes, a saturated ammonium chloride was added thereto, and a product was extracted with ethyl acetate. The organic layer was sequentially washed with a saturated ammonium chloride and with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate, and the solvents were distilled off under a reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2), to give 4.4 g (18%) of the captioned compound.

Provenance & Evidence