Water → 1-(3-Hydroxynaphthalen-2-yl)ethanone

HRID 228731ノート

反応式

HRID 228731 の反応式
COCN[C:5]([C:7]1[C:16]([OH:17])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:6].[CH3:18][Mg]Br.[Cl-].[NH4+].O>O1CCCC1>[OH:17][C:16]1[C:7]([C:5](=[O:6])[CH3:18])=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

参加物

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 13628209HCID 13628209、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 5988641-(3-Hydroxynaphthalen-2-yl)ethanone収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

3-Hydroxynaphthalene-2-carboxylic acid methoxymethylamide (600 mg) was dissolved in tetrahydrofuran (36 ml) to prepare a solution. A solution (9.8 ml) of 0.93 M methylmagnesium bromide in tetrahydrofuran was added thereto at −78° C., temperature of the mixture was raised to room temperature, and the mixture was stirred for 1.5 hr. A saturated aqueous ammonium chloride solution was added to stop the reaction, water was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with an aqueous potassium carbonate solution, was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-ethyl acetate to give 1-(3-hydroxynaphthalen-2-yl)-ethanone (378 mg, yield 78%).

後処理

  1. customto prepare a solution
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was then washed with an aqueous potassium carbonate solution
  5. washwas washed with water
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-822585761f4746eab6bafe44482be42d
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

反応ノート

読み込み中…