反応式
[Li+].CC([N-]C(C)C)C.C1COCC1.CCCCCCC.[CH2:21]([C:23]1[CH:28]=CC=C[CH:24]=1)C.[CH3:29][O:30][C:31](=[O:55])[CH2:32][C:33]1[CH:38]=[C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:36]=[C:35]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:34]=1.BrCC(C)=C>C1COCC1>[CH3:29][O:30][C:31](=[O:55])[CH:32]([C:33]1[CH:34]=[C:35]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:36]=[C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:38]=1)[CH2:24][C:23]([CH3:28])=[CH2:21]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
A 2M solution of LDA in THF-heptane-ethylbenzene (21.5 mL, 43.0 mmol) was added dropwise over 12 min to a stirred solution of (3,5-bis-benzyloxyphenyl)acetic acid methyl ester (13.0 g, 35.9 mmol) in THF (80 mL) at −78° C. under a nitrogen atmosphere. The temperature was maintained below −70° C. for a further 50 min then 3-bromo-2-methylpropene (4.0 mL, 39.7 mmol) was added in one portion and the reaction mixture was warmed to 0° C. After 2 h the mixture was concentrated in vacuo, diluted with sat. aq. NH4Cl (100 mL) and extracted with EtOAc (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), concentrated in vacuo and purified by flash chromatography (silica, 0-10% EtOAc in petroleum ether) to afford the title product as a yellow oil (14.1 g, 94%).
後処理
- temperatureThe temperature was maintained below −70° C. for a further 50 min
- concentrationAfter 2 h the mixture was concentrated in vacuo
- additiondiluted with sat. aq. NH4Cl (100 mL)
- extractionextracted with EtOAc (100 mL)
- washThe organic layer was washed with brine (100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- custompurified by flash chromatography (silica, 0-10% EtOAc in petroleum ether)
出典と根拠
- ORDレコード
- ord-e4cd3a373ea64c1397c60db3820a9fa0
- 出典データセット
- uspto-grants-2009_07
- 特許番号
- US07557244B2
関連ノート
読み込み中…