Ethylene Glycol → Ethyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetate

HRID 31654

反応式

HRID 31654 の反応式
[O:1]=[C:2]([CH2:9][CH3:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:11](O)[CH2:12][OH:13].C(OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C.CCCCCCC>[CH2:7]([O:6][C:4](=[O:5])[CH2:3][C:2]1([CH2:9][CH3:10])[O:13][CH2:12][CH2:11][O:1]1)[CH3:8]

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 78656Ethyl 3-oxovalerateHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 14244230Ethyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetate収率 58.9%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 8900Heptane溶媒

実験手順

A mixture of ethyl 3-oxopentanoate (5 g, 34.7 mmol), ethylene glycol (10.8 g, 174 mmol), triethyl orthoformate (5.14 g, 34.7 mmol), and p-toluenesulfonic acid monohydrate (598 mg, 3.14 mmol) was stirred at room temperature overnight. To the reaction mixture, heptane and ethyl acetate were added to dilute solution, which was washed with water. The organic layer was washed with a saturated saline solution, dried over magnesium sulfate, filtrated and the filtrate was concentrated under reduced pressure. The residue was dissolved in heptane and subjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/0→10/1) to obtain the title compound (3.85 g, yield: 58.9%) as colorless oil.

後処理

  1. washwas washed with water
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in heptane
  7. washsubjected to NH silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/0→10/1)

出典と根拠

ORDレコード
ord-0f477811c9694e35a09ec124018f0987
出典データセット
uspto-grants-2008_09
特許番号
US07425634B2

関連ノート

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