Dibenzylidene acetone → 1,5-Diphenylpentan-3-one

HRID 714195

반응식

HRID 714195 반응식
[C:1]1([CH:7]=[CH:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(OCC)(=O)C>[C:12]1([CH2:11][CH2:10][C:9](=[O:18])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

4

반응물 1

HCID 95417Dibenzylidene acetone

생성물 1

HCID 214961,5-Diphenylpentan-3-one수율 80%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

1,5-Diphenyl-1,4-pentadien-3-one (20b, 1.00 g, 4.3 mmol) and palladium on activated carbon (0.25 g, 5%) were combined in ethyl acetate (50 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 2 hr at room temperature. The resulting mixture was filtered through celite and the solvent evaporated to afford an oil. The crude oil was chromatographed on silica gel with ethyl acetate/hexane to give 0.82 g (80%) of a clear oil; 1H NMR: δ 2.76 (t, 4H, J=7.6 Hz), 2.97 (t, 4H, J=7.4 Hz), 7.30 (m, 10H); 13C NMR: δ 29.6, 44.2, 125.8, 128.0, 128.2, 140.7, 208.4.

후처리

  1. customfor 2 hr
  2. customat room temperature
  3. filtrationThe resulting mixture was filtered through celite
  4. customthe solvent evaporated
  5. customto afford an oil
  6. customThe crude oil was chromatographed on silica gel with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-ca9177fc33a24a53824c63853ffaeac3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187397B2

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