反応式
[F:1][C:2]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]2[CH:3]1[CH:4]=[CH:5][C:6]2=[O:8].C1(C)C=CC=CC=1.C([O:25]OO)(C)(C)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO>O>[O:25]1[CH:4]2[CH:5]1[C:6](=[O:8])[CH:7]1[CH:3]2[C:2]1([F:1])[C:9]([O:11][CH2:12][CH3:13])=[O:10]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
16.9 g of (1RS,5RS,6RS)ethyl 6-fluoro-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylate was dissolved into 100 ml of toluene. 30.6 ml of 70% t-butylhydroxyperoxide aqueous solution and 11.5 ml of 10% benzyltrimethylammoniumhydroxide/methanol solution were added thereto, and this was stirred at room temperature for 4 hours. After the reaction solution was poured into water, it was extracted twice with ethyl acetate. The obtained organic layers were consolidated to be washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After filtering off the desiccant, concentration of the filtrate was carried out under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=8:1 to 6:1), yielding 13.4 g of (1RS,3RS,4RS,5SR,6RS)ethyl 3,4-epoxy-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate. The proton NMR and mass spectrograph data are shown below.
後処理
- extractionwas extracted twice with ethyl acetate
- washto be washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- filtrationAfter filtering off the desiccant, concentration of the filtrate
- customThe residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=8:1 to 6:1)
出典と根拠
- ORDレコード
- ord-a6764721e7ea448e9f1e1bc5ddfc12ce
- 出典データセット
- uspto-grants-2001_12
- 特許番号
- US06333428B1
関連ノート
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