反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](=[C:14](\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[CH2:15][OH:16])/[CH2:12][OH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].N1C=CN=C1.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C1COCC1.ClCCl.[Cl-].[Na+].O>[Si:32]([O:16][CH2:15]/[C:14](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[C:11](/[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1)\[CH2:12][OH:13])([C:29]([CH3:31])([CH3:30])[CH3:28])([CH3:34])[CH3:33]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- -78 °C
実験手順
To a solution of 110 g of (2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol and of imidazole in 1 L of THF stirred at −78° C., a solution 51 g of TBSCl in 250 mL of dichloromethane was added dropwise. The resulting mixture was stirred at −78° C. 0.5 hr. Brine was then added and then warmed to room temperature. The organic phase was separated and the aqueous phase was extracted with EtOAc. The organic phases were combined and dried over Na2SO4 and evaporated. The resulting crude material was purified by flash chromatography to afford 25.6 g of the title compound as a white solid. 1H NMR (acetone-d6, 500 M Hz): δ 7.69 (d, 2H), 7.37 (d, 2H), 7.18–7.04 (m, 5H), 4.77 (s, 2H), 4.65 (d, 2H), 3.96 (t, 1H, OH), 3.03 (s, 3H), 0.84 (s, 9H), 0.01 (s, 6H).
後処理
- custom0.5 hr
- temperaturewarmed to room temperature
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with EtOAc
- dry with materialdried over Na2SO4
- customevaporated
- customThe resulting crude material was purified by flash chromatography
出典と根拠
- ORDレコード
- ord-b541e7ac25584af28eed67fe53b63920
- 出典データセット
- uspto-grants-2007_01
- 特許番号
- US07169809B2
関連ノート
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