Ethyl (E)-3-(5,6-Dihydro-2H-pyran-3-yl)acrylate → Ethyl 3-(tetrahydro-2H-pyran-3-yl)propanoate

HRID 1011035노트

반응식

HRID 1011035 반응식
[O:1]1[CH2:6][CH2:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2]1.[H][H]>[Pd].C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2]1

참가 물질

5

반응물 2

HCID 12872207Ethyl (E)-3-(5,6-Dihydro-2H-pyran-3-yl)acrylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 15676000Ethyl 3-(tetrahydro-2H-pyran-3-yl)propanoate수율 174.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

The above was repeated in the exact same fashion with a second batch. Hence a solution of ethyl (2E)-3-(5,6-dihydro-2H-pyran-3-yl)-2-propenoate (2.59 g) and palladium on carbon (147 mg, 10% wet) in ethyl acetate (65 ml) was hydrogenated at atmospheric pressure and room temperature. The hydrogen uptake (˜715 ml) was complete after 15 minutes. The catalyst was filtered through celite and the filtrate concentrated in vacuo. to afford a pale yellow oil which was combined with that of the first batch (5.34 g). This was purified by silica chromatography (120 g) (ISCO) using a gradient elution of 0-10% cyclohexane:ethyl acetate to afford the title compound as a clear oil (4.61 g).

후처리

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. filtrationThe catalyst was filtered through celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customto afford a pale yellow oil which
  5. customThis was purified by silica chromatography (120 g) (ISCO)
  6. washa gradient elution of 0-10% cyclohexane

출처 및 근거

ORD 기록
ord-a4f6d683d3d74d0a89fc9a609469df5f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977344B2

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