반응 #2286316
ord-2d9ad3320eb34c8f9a830cd135a5c1c5
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후처리
- 1workup.STIRRINGAfter stirring 30 min at room temperature
- 2기타the reaction was cautiously quenched by addition to a 1:1 mixture of a saturated aqueous sodium chloride solution (30 mL)
- 3추출The mixture was extracted with ethyl acetate (3×50 mL)
- 4세척washed with a saturated aqueous sodium chloride solution (20 mL)
- 5건조dried with magnesium sulfate
- 6여과filtered
- 7농축concentrated under vacuum
- 8기타The resulting solid was dried under high vacuum
실험 절차
A mixture of 3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-benzoic acid methyl ester (52) (160 mg, 0.45 mmol) in tetrahydrofuran (5 mL) at 25° C. was treated with a 1M solution of diisobutylaluminum hydride in tetrahydrofuran (2.7 mL, 2.7 mmol). The reaction was stirred at room temperature for 24 h. A TLC of the reaction indicated that starting material was still present. An additional amount of the 1 M solution of diisobutylaluminum hydride in tetrahydrofuran (1.0 mL) was added to the reaction. After stirring 30 min at room temperature, the reaction was cautiously quenched by addition to a 1:1 mixture of a saturated aqueous sodium chloride solution (30 mL) and a 2N aqueous hydrochloric acid solution (30 mL). The mixture was extracted with ethyl acetate (3×50 mL). The organic layers were combined, washed with a saturated aqueous sodium chloride solution (20 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting solid was dried under high vacuum to afford 6-(2,6-dichloro-4-hydroxymethyl-benzyl)-4-isopropyl-pyridazin-3-one (53) (168 mg) as a brown solid that was used without further purification; LRMS-ES(+) for C15H16Cl2N2O2 (M+H) m/z=327. MW=327.2130, Exact Mass=326.0589