Benzophenone → (4S,5S)-5-((benzyloxy)methyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2(3H)-one
反応式
[CH2:1]([O:8][CH2:9][C@H:10]1[O:14][C:13](=[O:15])[CH:12]=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.[O:30]1[CH2:34][CH2:33][O:32][CH2:31]1>>[CH2:1]([O:8][CH2:9][C@H:10]1[O:14][C:13](=[O:15])[CH2:12][C@@H:11]1[CH:31]1[O:32][CH2:33][CH2:34][O:30]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1参加物
反応条件
- 温度
- 0 °C
実験手順
A solution of furanone (13) (1.2 g, 5.88 mmols) and benzophenone (108 mg, 0.588 mmols) in [1,3]-dioxolane (108 mg) was degassed for 40 min in a stream of argon. The mixture then was irradiated using one 450 watt ACE glass medium pressure mercury lamp, from a distance of 15 cm, for 9 hours. Progress of this reaction was observed via 1H-NMR. As the reaction mixture was degassed, and throughout all of the irradiation time, the reaction flask was held in a water cooled cooling mantel. The temperature of the cooling water was constantly maintained near 0° C. Upon completion of the reaction, solvent was removed under reduced pressure, followed by column chromatography on silica gel (35% EtOAc in hexanes as the eluent), yielding the title compound (1.34 g, 82%) as a clear oil, Rf=0.14 (30% EtOAc in hexanes), [α]25D 16.5° (c 1.2, CHCl3); 1H-NMR (500 MHz, CDCl3) δ: 2.50 (dd, 1H, J=3.9, 12.9 Hz), 2.70-2.79 (m, 2H), 3.58 (dd, 1H, J=3.5, 7.2 Hz), 3.75 (dd, 1H, J=2.8, 7.9 Hz), 3.87-3.92 (m, 2H), 3.97-4.00 (m, 2H), 4.51 (d, 1H, J=11.9 Hz), 4.57-4.61 (m, 2H), 4.88 (d, 1H, J=3.6 Hz), 7.26-7.36 (m, 5H); 13C-NMR (125.8 MHz, CDCl3) δ: 30.39, 40.53, 65.77, 71.74, 73.99, 79.52, 104.14, 128.00, 128.89, 138.07, 176.79.
後処理
- customThe mixture then was irradiated
- customAs the reaction mixture was degassed
- temperaturecooled
- temperaturecooling mantel
- customUpon completion of the reaction, solvent
- customwas removed under reduced pressure
出典と根拠
- ORDレコード
- ord-915fa9affd1a4a499aa4a5ec4ecf93f4
- 出典データセット
- uspto-grants-2005_07
- 特許番号
- US06919465B2
反応ノート
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