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

HRID 228731노트

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HRID 228731 반응식
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

참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 13628209HCID 13628209, 화합물HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 5988641-(3-Hydroxynaphthalen-2-yl)ethanone수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-822585761f4746eab6bafe44482be42d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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