Water → HCID 18770243、化合物

HRID 1792387ノート

反応式

HRID 1792387 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C([Li])CCC.[CH3:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28](=[O:42])[CH:29]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[CH2:30][S:31]2)=[CH:26][CH:25]=1.O>O1CCCC1>[Si:7]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([C:28]2([OH:42])[C:27]3[C:32](=[CH:33][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[S:31][CH2:30][CH:29]2[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[CH:16]=[CH:15][CH:14]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

参加物

6

反応物 4

HCID 962WaterHCID 111303687-Methoxy-3-(4-methoxyphenyl)thiochroman-4-oneHCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 18770243HCID 18770243、化合物収率 28.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (3-bromobenzyloxy)-t-butyldimethylsilane (2.207 g, 7.326 mmol) in dry tetrahydrofuran (20 ml) was added n-butyl lithium (4.18 ml, 6.66 mmol, 1.59M tetrahydrofuran solution) at −78° C. over 25 minutes and stirred for 50 minutes. Then to the reaction mixture was added 7-methoxy-3-(4-methoxyphenyl)thiochroman-4-one (1 g, 3.33 mmol) dissolved in tetrahydrofuran at the same temperature over 10 minutes. The reaction mixture was stirred for 20 minutes at −78° C., followed at −15° C. for 12 h and at 0° C. for 8 h. When the reaction was completed, water was added to the reaction solution which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane:ethyl acetate=8:2) to give 0.49 g (yield: 28%) of the title compound as a colorless oil. In this reaction 0.55 g (55%) of the unreacted starting compound was recovered.

後処理

  1. stirringThe reaction mixture was stirred for 20 minutes at −78° C.
  2. waitfollowed at −15° C. for 12 h and at 0° C. for 8 h
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=8:2)

出典と根拠

ORDレコード
ord-183140d4111443ef90741e80372e6977
出典データセット
uspto-grants-2006_07
特許番号
US07074819B2

反応ノート

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