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Hydrochloric Acid → Benzyl 4-(2-cyclohexylethoxy)acetoacetate

HRID 397971
ノート
印刷プレビュー

反応式

HRID 397971 の反応式
[H-].[Na+].[CH:3]1([CH2:9][CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[CH2:13][C:14](=[O:26])[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].Cl>C1COCC1>[CH:3]1([CH2:9][CH2:10][O:11][CH2:13][C:14](=[O:26])[CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]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

6

反応物 4

HCID 313Hydrochloric AcidHCID 205082-CyclohexylethanolHCID 24758Sodium hydrideHCID 15540594Benzyl 4-chloro-3-oxobutanoate

生成物 1

HCID 15540595Benzyl 4-(2-cyclohexylethoxy)acetoacetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

0.68 g (17.0 mmol) of sodium hydride (60% oily) was suspended in 7 ml of THF. 1.36 g (10.6 mmol) of 2-cyclohexylethanol was added to the obtained suspension at 0° C., and they were stirred at 40° C. for 30 minutes. 2.00 g (8.82 mmol) of benzyl 4-chloroacetoacetate was added to the obtained mixture at room temperature, and they were refluxed at 100° C. for 3 hours. 1 N hydrochloric acid was added to the reaction mixture. After the extraction with ethyl acetate, the organic layer was washed with 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=4/1) to obtain the title compound.

後処理

  1. temperaturethey were refluxed at 100° C. for 3 hours
  2. extractionAfter the extraction with ethyl acetate
  3. washthe organic layer was washed with 10% aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-7ed86e6a728b43a69e891c480f8699b4
出典データセット
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06610717B2

反応ノート

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