2-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-one → 2-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol

HRID 455687

反応式

HRID 455687 の反応式
[CH:1]([Mg]Cl)=[CH2:2].[CH3:5][O:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([C:21]4[CH:22]=[N:23][CH:24]=[N:25][CH:26]=4)=[CH:14][CH:15]=3)[C:10](=[O:27])[C:9]=2[CH:8]=1>C1COCC1>[CH3:5][O:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([C:21]4[CH:26]=[N:25][CH:24]=[N:23][CH:22]=4)=[CH:14][CH:15]=3)[C:10]([CH:1]=[CH2:2])([OH:27])[C:9]=2[CH:8]=1

参加物

4

反応物 2

HCID 574756542-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-oneHCID 178461836HCID 178461836、化合物

生成物 1

HCID 574756552-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

A solution of vinylmagnesium chloride (1.6M solution in THF; 0.82 mL, 1.314 mmol) was added dropwise to a solution of 2-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-one (200 mg, 0.657 mmol) in THF (10 mL) at −78° C. After 30 min, the reaction mixture was allowed to warm to −10° C. and was then quenched with saturated aqueous ammonium chloride. The reaction was extracted with EtOAc, and the organic phase was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography to give 2-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol as a pale yellow gum.

後処理

  1. customwas then quenched with saturated aqueous ammonium chloride
  2. extractionThe reaction was extracted with EtOAc
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-384740b203e645908800479fe166b8b2
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

関連ノート

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