Water → 4-[3-(1,3-Dioxolan-2-yl)-phenyl]-7-methoxy-3-(4-methoxyphenyl)thiochroman-4-ol

HRID 1792386ノート

反応式

HRID 1792386 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH3:18][O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24](=[O:38])[CH:25]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH2:26][S:27]2)=[CH:22][CH:21]=1.O>O1CCCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[CH:3]=[C:2]([C:24]2([OH:38])[C:23]3[C:28](=[CH:29][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[S:27][CH2:26][CH:25]2[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 111303687-Methoxy-3-(4-methoxyphenyl)thiochroman-4-oneHCID 178418339Butyllithium

生成物 1

HCID 220331164-[3-(1,3-Dioxolan-2-yl)-phenyl]-7-methoxy-3-(4-methoxyphenyl)thiochroman-4-ol収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(3-bromophenyl)-1,3-dioxolane (3.04 g, 13.28 mmol) in dry tetrahydrofuran (35 ml) was added n-butyl lithium (8.37 ml, 13.316 mmol, 1.59 mol/l tetrahydrofuran solution) dropwise as −78° C. over 10 minutes and stirred for 50 minutes at the same temperature. Then to the reaction mixture was added 7-methoxy-3-(4-methoxyphenyl)thiochroman-4-one (2 g, 6.658 mmol) dissolved in tetrahydrofiuran at the same temperature over 10 minutes. The reaction mixture was stirred for 6 h at −78° C. and followed at −10C for 2 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=8:1 to 7:3) to give 1.50 g (yield: 50%) of the title compound as a colorless oil. In this reaction, 0.77 g (38%) of the unreacted starting compound was recovered.

後処理

  1. dissolutiondissolved in tetrahydrofiuran at the same temperature over 10 minutes
  2. stirringThe reaction mixture was stirred for 6 h at −78° C.
  3. custom−10C for 2 h
  4. extractionwas then extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=8:1 to 7:3)

出典と根拠

ORDレコード
ord-a7f5d06a6ac7405898a9e00a73e7a97e
出典データセット
uspto-grants-2006_07
特許番号
US07074819B2

反応ノート

読み込み中…