4-Toluenesulfonyl chloride → (+/-)-(7-Nitro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate
反応式
[N+:1]([C:4]1[C:12]2[O:11][CH:10]([CH2:13][OH:14])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:14][CH2:13][CH:10]2[CH2:9][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=3[O:11]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1参加物
実験手順
To a solution of (±)-(7-nitro-2,3-dihydro-1-benzofuran-2-yl)methanol (3.14 g, 16.09 mol) in dichloromethane (100 mL) was added diisopropylethyl amine (4.16 g, 32.18 mmol), N,N-dimethylaminopyridine (0.39 g, 3.2 mmol), and p-toluenesulfonyl chloride (4.6 g, 24.13 mmol) the reaction was allowed to stir at room temperature for 12 h. The reaction was diluted with dichloromethane (500 mL), washed with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous sodium chloride (200 mL), dried (magnesium sulfate) and the solvent removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, dichloromethane: hexanes 3:10) afforded 5.2 g (94%) of (±)-(7-nitro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as off-white solid. mp 129-131° C.
後処理
- washwashed with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous sodium chloride (200 mL)
- dry with materialdried (magnesium sulfate)
- customthe solvent removed in vacuo
- customto give a crude oil
- customPurification by flash column chromatography (silica, dichloromethane: hexanes 3:10)
出典と根拠
- ORDレコード
- ord-423c347516624bbfa48f9d5e2c0b7b91
- 出典データセット
- uspto-grants-2008_10
- 特許番号
- US07435837B2
反応ノート
読み込み中…