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Water → 1-[3-(3-Methoxypropoxy)-5-methylphenyl]ethanone

HRID 922450
ノート
印刷プレビュー

反応式

HRID 922450 の反応式
C(O[C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=[C:7]([C:14](OCC)=O)[CH:6]=1)(=O)C.[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH3:25]B1OB(C)OB(C)O1.O.[O:35]1[CH2:40]COC[CH2:36]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:36][O:35][CH2:40][CH2:11][CH2:12][O:13][C:9]1[CH:10]=[C:5]([C:19](=[O:22])[CH3:25])[CH:6]=[C:7]([CH3:14])[CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 675451626-Benzofurancarboxylic acid, 4-(acetyloxy)-, ethyl ester

生成物 1

HCID 683105641-[3-(3-Methoxypropoxy)-5-methylphenyl]ethanone

試薬・触媒・溶媒 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒

反応条件

温度
110 °C

実験手順

To a solution of the compound obtained in the (1) (8.22 g) in 1,4-dioxane 9100 mL) were added potassium carbonate (8.6 g), trimethylboroxine (3.5 mL) and 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium (II) (1.51 g), and the mixture was heated to stir at 110° C. for 2 hours. After cooling to room temperature, thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=5/1) to give 1-[3-(3-methoxypropoxy)-5-methylphenyl]ethanone [REx(21-2)] (4.15 g) as a brown oil.

後処理

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-094b9d722302499786841d5949b24691
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278944B2

反応ノート

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