2,6-Dimethyl-4-pyranone → cis-2,6-dimethyloxan-4-one

HRID 595237

반응식

HRID 595237 반응식
[CH3:1][C:2]1[O:3][C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1>C(O)C>[CH3:1][C@H:2]1[CH2:7][C:6](=[O:8])[CH2:5][C@@H:4]([CH3:9])[O:3]1

참가 물질

3

반응물 1

HCID 138622,6-Dimethyl-4-pyranone

생성물 1

HCID 10441716cis-2,6-dimethyloxan-4-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2,6-Dimethyl-4H-pyran-4-one (2.0 g, 16 mmol) was dissolved in ethanol (10 mL) and purged under nitrogen. Palladium on carbon (5%, 200 mg) was then added and the reaction mixture stirred under hydrogen gas (40 psi) for 24 hours. The reaction mixture was filtered over CELITE, rinsed with ethanol, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (5 to 30% EtOAc/hexanes) to afford cis-2,6-dimethyltetrahydro-4H-pyran-4-one as a colorless liquid. 1H NMR (500 MHz, CDCl3) δ 3.77-3.70 (m, 2H), 2.38-2.32 (m, 2H), 2.25-2.20 (m, 2H), 1.32 (d, J=6.1 Hz, 6H).

후처리

  1. custompurged under nitrogen
  2. additionPalladium on carbon (5%, 200 mg) was then added
  3. filtrationThe reaction mixture was filtered over CELITE
  4. washrinsed with ethanol
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (5 to 30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-548681de6ecf476bb6684ed4cbec266e
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242984B2

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