Hydrochloric Acid → Ethylcyclohexyl(oxo)acetate

HRID 471803

反応式

HRID 471803 の反応式
[Mg].[CH:2]1(Br)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:9]([O:11][C:12](=[O:18])[C:13](OCC)=[O:14])[CH3:10].Cl>C1COCC1>[CH:2]1([C:13](=[O:14])[C:12]([O:11][CH2:9][CH3:10])=[O:18])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 7960Cyclohexyl bromideHCID 5462224Magnesium

生成物 1

HCID 11041407Ethylcyclohexyl(oxo)acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of magnesium turnings (2.20 g, 90.32 mmol) in THF (100 mL) was added cyclohexyl bromide (9.27 mL, 75.27 mmol). The mixture was sonicated (note 1) for 30 min, the supernatant liquid was decanted into an addition funnel and added to a solution of diethyloxalate (22.0 g, 146.14 mmol) in THF (240 mL) at −10° C. over one hour. After 30 minutes, 10% HCl (75 mL) was added the mixture was and stirred 15 minutes. Layers were separated and the aqueous layer was extracted with Et2O (100 mL). Combined organics were washed (brine), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.15-1.40 (m, 5H) 1.56-1.94 (m, 8H) 2.97-3.05 (m, 1H) 4.30 (q, J=7.32 Hz, 2H).

後処理

  1. customThe mixture was sonicated (note 1) for 30 min
  2. customthe supernatant liquid was decanted into an addition funnel
  3. customLayers were separated
  4. extractionthe aqueous layer was extracted with Et2O (100 mL)
  5. washCombined organics were washed (brine)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ecec9907c0f64ee8bb47f10ab05bec18
出典データセット
uspto-grants-2014_01
特許番号
US08633175B2

関連ノート

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