Hydrochloric Acid → Ethylcyclohexyl(oxo)acetate

HRID 70270

반응식

HRID 70270 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 11041407Ethylcyclohexyl(oxo)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6f51c43067ae4e91a6de6452c478b179
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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