反応式
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][SH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:16][CH2:17][C:18]([OH:20])=[O:19].Cl>CN(C=O)C.O>[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][S:12][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1参加物
実験手順
A solution of 2-[2-phenylethoxy]ethane thiol (2.13 g) in dry DMF (10 ml) was added dropwise to a cooled (0°) stirred suspension of sodium hydride (0.60 g, 80% in oil) in DMF (50 ml). The mixture was stirred at 0° for 90 min. A solution of 3-bromopropanoic acid (3.15 g) in dry DMF (10 ml) was then added dropwise and the reaction was stirred at room temperature for 16 hours. Water (250 ml) was added and the whole was acidified to pH 2/3 with concentrated hydrochloric acid. The aqueous solution was extracted several times with ether and the combined ethereal layers were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. This yielded the crude acid which was purified by flash chromatography over silica using 6:1 dichloromethane:ether (1 drop acetic acid/100 ml of eluant) to give the subtitled compound (2.15 g).
後処理
- temperaturea cooled (0°)
- stirringThe mixture was stirred at 0° for 90 min
- stirringthe reaction was stirred at room temperature for 16 hours
- extractionThe aqueous solution was extracted several times with ether
- washthe combined ethereal layers were washed with water and brine
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
- customThis yielded the crude acid which
- customwas purified by flash chromatography over silica using 6:1 dichloromethane
出典と根拠
- ORDレコード
- ord-045f6311451245aeab0e5fac0928da69
- 出典データセット
- uspto-grants-1997_07
- 特許番号
- US05648370
関連ノート
読み込み中…